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[ CAS No. 63675-74-1 ] {[proInfo.proName]}

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Chemical Structure| 63675-74-1
Chemical Structure| 63675-74-1
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Product Details of [ 63675-74-1 ]

CAS No. :63675-74-1 MDL No. :MFCD02083138
Formula : C16H14O2S Boiling Point : -
Linear Structure Formula :- InChI Key :HRWAGCVMOGWQJF-UHFFFAOYSA-N
M.W : 270.35 Pubchem ID :850941
Synonyms :

Safety of [ 63675-74-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 63675-74-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 63675-74-1 ]

[ 63675-74-1 ] Synthesis Path-Downstream   1~4

  • 1
  • aqueous sodium chloride [ No CAS ]
  • [ 63675-74-1 ]
  • [ 84449-80-9 ]
  • [ 82640-04-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; thionyl chloride; ethanethiol;aluminium trichloride; In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water; chlorobenzene; EXAMPLE 3 6-hydroxy-2-(4-hydroxyphenyl)-3[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride Under a nitrogen blanket, a mixture of 3 g. of 4-(2-piperidinoethoxy) benzoic acid, hydrochloride, 2 drops of dimethylformamide, 2.5 ml. of thionyl chloride and 40 ml. of chlorobenzene was heated at 70°-75° C. for about one hour. The excess thionyl chloride and 15-20 ml. of solvent were then distilled off. The remaining suspension was cooled to ambient temperature, and to it were added 100 ml. of dichloromethane, 2.7 g. of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene and 10 g. of aluminum chloride. The solution was stirred for about one hour, 7.5 ml. of ethanethiol was added, and the mixture was stirred for 45 minutes more. Then 40 ml. of tetrahydrofuran was added, followed by 15 ml. of 20percent hydrochloric acid, with an exotherm to reflux. Fifty ml. of water and 25 ml. of saturated aqueous sodium chloride were added. The mixture was stirred and allowed to cool to ambient temperature. The precipitate was collected by filtration and washed successively with 30 ml of water, 40 ml of 25percent aqueous tetrahydrofuran, and 35 ml. of water. The solids were then dried at 40° C. under vacuum to obtain 5.05 g. of product, which was identified by nmr. delta1.7(6H, m, N(CH2 CH2)2 CH2); 2.6-3.1 (2H, m, NCH2); 3.5-4.1 (4H, m, NCH2); 4.4 (2H, m, OCH2); 6.6-7.4 (9H, m, aromatic); 7.7 (2H, d, aromatic o to CO); 9.8(2H, m, OH).
With hydrogenchloride; thionyl chloride; ethanethiol;aluminium trichloride; In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water; chlorobenzene; PREPARATION 3 6-hydroxy-2-(4-hydroxyphenyl)-3[-4-(2piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride Under a nitrogen blanket, a mixture of 3 g. of 4-(2piperidinoethoxy)benzoic acid, hydrochloride, 2 drops of dimethylformamide, 2.5 ml. of thionyl chloride and 40 ml. of chlorobenzene was heated at 70°-75° C. for about one hour. The excess thionyl chloride and 15-20 ml. of solvent were then distilled off. The remaining suspension was cooled to ambient temperature, and to it were added 100 ml. of dichloromethane, 2.7 g. of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene and 10 g. of aluminum chloride. The solution was stirred for about one hour, 7.5 ml. of ethanethiol was added, and the mixture was stirred for 45 minutes more. Then 40 ml. of tetrahydrofuran was added, followed by 15 ml. of 20percent hydrochloric acid, with an exotherm to reflux. Fifty ml. of water and 25 ml. of saturated aqueous sodium chloride were added. The mixture was stirred and allowed to cool to ambient temperature. The precipitate was collected by filtration and washed successively with 30 ml. of water, 40 ml of 25percent aqueous tetrahydrofuran, and 35 ml. of water. The solids were then dried at 40° C. under vacuum to obtain 5.05 g. of product, which was identified by nmr. delta1.7(6H, m, N(CH2 CH2)2 CH2); 2.6-3.1(2H, m, NCH2); 3.5-4.1 (4H, m, NCH2); 4.4(2H, m, OCH2); 6.6-7.4(9H, m, aromatic); 7.7(2H, d, aromatic o to CO); 9.8(2H, m, OH).
With hydrogenchloride; thionyl chloride; ethanethiol;aluminium trichloride; In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water; chlorobenzene; EXAMPLE 1 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride Under a nitrogen blanket, a mixture of 3 g. of 4-(2-piperidinoethoxy)benzoic acid, hydrochloride, 2 drops of dimethylformamide, 2.5 ml. of thionyl chloride and 40 ml. of chlorobenzene was heated at 70°-75° C. for about one hour. The excess thionyl chloride and 15-20 ml. of solvent were then distilled off. The remaining suspension was cooled to ambient temperature, and to it were added 100 ml. of dichloromethane, 2.7 g. of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene and 10 g. of aluminum chloride. The solution was stirred for about one hour, 7.5 ml. of ethanethiol was added, and the mixture was stirred for 45 minutes more. Then 40 ml. of tetrahydrofuran was added, followed by 15 ml. of 20percent hydrochloric acid, with an exotherm to reflux. Fifty ml. of water and 25 ml. of saturated aqueous sodium chloride were added. The mixture was stirred and allowed to cool to ambient temperature. The precipitate was collected by filtration and washed successively with 30 ml. of water, 40 ml. of 25percent aqueous tetrahydrofuran, and 35 ml. of water. The solids were then dried at 40° C. under vacuum to obtain 5.05 g. of product, which was identified by its nmr spectrum, using a 90 mHz instrument and deuterochloroform. delta1.7 (6H, m, N(CH2 CH2)2 CH2); 2.6-3.1 (2H, m, NCH2); 3.5-4.1 (4H, m, NCH2); 4.4 (2H, m, OCH2); 6.6-7.4 (9H, m, aromatic); 7.7(2H, d, aromatic o to CO); 9.8 (2H, m, OH).
With hydrogenchloride; thionyl chloride; ethanethiol;aluminium trichloride; In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water; chlorobenzene; EXAMPLE 1 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride Under a nitrogen blanket, a mixture of 2 g. of 4-(2-piperidinoethoxy)benzoic acid, hydrochloride, 2 drops of dimethylformamide, 2.5 ml. of thionyl chloride and 40 ml. of chlorobenzene was heated at 70°-75° C. for about one hour. The excess thionyl chloride and 15-20 ml. of solvent were then distilled off. The remaining suspension was cooled to ambient temperature, and to it were added 100 ml. of dichloromethane, 2.7 g. of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene and 10 g. of aluminum chloride. The solution was stirred for about one hour, 7.5 ml. of ethanethiol was added, and the mixture was stirred for 45 minutes more. Then 40 ml. of tetrahydrofuran was added, followed by 15 ml. of 20percent hydrochloric acid, with an exotherm to reflux. Fifty ml. of water and 25 ml. of saturated aqueous sodium chloride were added. The mixture was stirred and allowed to cool to ambient temperature. The precipitate was collected by filtration and washed successively with 30 ml. of water, 40 ml. of 25percent aqueous tetrahydrofuran, and 35 ml. of water. The solids were then dried at 40° under vacuum to obtain 5.05 g. of crude product, which was identified by its nmr spectrum, using a 90 mHz instrument and deuterochloroform. delta1.7 (6H, m, N(CH2 CH2)2 CH2); 2.6-3.1 (2H, m, NCH2); 3.5-4.1 (4H, m, NCH2); 4.4 (2H, m, OCH2); 6.6-7.4 (9H, m, aromatic); 7.7(2H, d, aromatic o to CO); 9.8 (2H, m, OH).
With hydrogenchloride; CO; thionyl chloride; ethanethiol;aluminium trichloride; In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water; chlorobenzene; EXAMPLE 8 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride Under a nitrogen blanket, a mixture of 3 g. of 4-(2-piperidinoethoxy)benzoic acid, hydrochloride, 2 drops of dimethylformamide, 2.5 ml. of thionyl chloride and 40 ml. of chlorobenzene was heated at 70°-75° C. for about one hour. The excess thionyl chloride and 15-20 ml. of solvent were then distilled off. The remaining suspension was cooled to ambient temperature, and to it were added 100 ml. of dichloromethane, 2.7 g. of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene and 10 g. of aluminum chloride. The solution was stirred for about one hour, 7.5 ml. of ethanethiol was added, and the mixture was stirred for 45 minutes more. Then 40 ml. of tetrahydrofuran was added, followed by 15 ml. of 20percent hydrochloric acid, with an exotherm to reflux. Fifty ml. of water and 25 ml. of saturated aqueous sodium chloride was added. The mixture was stirred and allowed to cool to ambient temperature. The precipitate was collected by filtration and washed successively with 30 ml. of water, 40 ml. of 25percent aqueous tetrahydrofuran, and 35 ml. of water. The solids were then dried at 40° C. under vacuum to obtain 5.05 g. of product, which was identified by nmr. delta1.7 (6H, m, N(CH2 CH2)2 CH2); 2.6-3.1 (2H, m, NCH2); 3.5-4.1 (4H, m, NCH2); 4.4 (2H, m, OCH2); 6.6-7.4 (9H, m, aromatic); 7.7 (2H, d, aromatic o to CO); 9.8 (2H, m, OH). The following group of examples illustrates the preparation of ester derivatives of this invention from the dihydroxy compound.

  • 2
  • [ 63675-74-1 ]
  • [ 84449-80-9 ]
  • [ 82640-04-8 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; ethanethiol;aluminium trichloride; In tetrahydrofuran; N-methyl-acetamide; dichloromethane; chlorobenzene; EXAMPLE 11 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride A mixture of 1.5 g. of 4-(2-piperidinoethoxy)benzoic acid, hydrochloride, 20 ml. of chlorobenzene, 3 ml. of thionyl chloride and 2 drops of dimethylformamide was stirred at 75°-79° for 2 hours, to prepare the corresponding acid chloride. Vacuum was then applied, and the temperature dropped to 65°. Distillation was continued until the pot temperature was 90°. Twenty ml. of additional chlorobenzene was added, and the mixture was redistilled to a pot temperature of 90°, and was then cooled. To the mixture was added 15 ml. of dichloromethane, 1.35 g. of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene, 5 g. of aluminum chloride and 15 ml. of additional dichloromethane. The mixture was stirred at 27°-29° for 90 minutes, and then 1.6 ml. of ethanethiol was added. The mixture was stirred with cooling to maintain it at or below 35°. After 30 minutes, the mixture was worked up as described in Example 8 above, except that only 18 ml. of tetrahydrofuran and of water were used, to obtain 2.6 g. of the crude desired product, m.p. 217°, which was found to be substantially identical to the product of Example 1 by nmr and thin layer chromatography.
With thionyl chloride; ethanethiol;aluminium trichloride; In tetrahydrofuran; N-methyl-acetamide; dichloromethane; chlorobenzene; EXAMPLE 16 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride A mixture of 1.5 g. of 4-(2-piperidinoethoxy)-benzoic acid, hydrochloride, 20 ml. of chlorobenzene, 3 ml. of thionyl chloride and 2 drops of dimethylformamide was stirred at 75°-79° for 2 hours, to prepare the corresponding acid chloride. Vacuum was then applied, and the temperature dropped to 65°. Distillation was continued until the pot temperature was 90°. Twenty ml. of additional chlorobenzene was added, and the mixture was redistilled to a pot temperature of 90°, and was then cooled. To the mixture was added 15 ml. of dichloromethane, 1.35 g. of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene, 5 g. of aluminum chloride and 15 ml. of additional dichloromethane. The mixture was stirred at 27°-29° for 90 minutes, and then 1.6 ml. of ethanethiol was added. The mixture was stirred with cooling to maintain it at or below 35°. After 30 minutes, the mixture was worked up as described in Example 8 above, except that only 18 ml. of tetrahydrofuran and of water were used, to obtain 2.6 g. of the crude desired product, m.p. 217°, which was found to be substantially identical to the product of Example 8 by nmr and thin layer chromatography.
Example 13 Preparation of Raloxifene Hydrochloride [6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzyl]benzo[b]Thiophene Hydrochloride] Under a nitrogen blanket, a mixture of 3 g of 4-(2-piperidinoethoxy)benzoic acid, hydrochloride, 2 drops of dimethylformamide, 2.5 mL of thionyl chloride and 40 mL of chlorobenzene was heated at 70° C.-75° C. for about 1 hour. The excess thionyl chloride and 15-20 mL solvent were then distilled off. The remaining suspension was cooled to ambient temperature and to it were added 100 mL of dichloromethane, 2.7 g of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene (preparation of which is described in Example 14) and 10 g of aluminum chloride. After the solution was stirred for about 1 hour, 7.5 mL of ethanethiol was added, and the mixture was stirred for an additional 45 minutes. Then 40 mL of tetrahydrofuran was added, followed by 15 mL of 20percent hydrochloric acid, with an exotherm to reflux. 50 mL of water and 25 mL of saturated aqueous sodium chloride were added. The mixture was stirred and allowed to cool to ambient temperature. The precipitate was collected by filtration and washed successively with 30 mL of water, 40 mL of 25percent aqueous tetrahydrofuran and 35 mL of water. The solids were then dried at 40° C. under vacuum to obtain 5.05 g of product, which was identified by nuclear magnetic resonance as (6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-peridinoethoxy)benzyl]benzo[b]thiophene hydrochloride).
4-(2-Piperidinoethoxy)-benzoic acid hydrochloride (120 gm) was added to toluene (600 ml) and then added dimethylformamide (2 ml) and thionyl chloride (160 gm) under stirring. The temperature of the reaction mass was raised to 80°C and maintained for 2 hours. The reaction mass was distilled off solvent completely under vacuum at 65° to obtain residue. To the residue was added methylene chloride (1500 ml) and then added 6-methoxy-2-(4-methoxyphenyl)-benzo[b]-thiophene (100 gm). To the reaction mass was added aluminum chloride (360 gm) for 1 hour and maintained for 2 hours at room temperature. The reaction mass was cooled to 10°C and then added propanethiol (100 ml) for 1 hour 30 minutes under stirring. The temperature of the reaction mass was gradually raised to room temperature and maintained for 1 hour 30 minutes. The reaction mass was cooled to 5°C and then added methanol (600 ml). The reaction mass was stirred for 30 minutes at 5 C and then added dilute hydrochloric acid (2N, 800 ml). To the reaction mass was added saturated sodium chloride solution (800 ml) and water (800 ml). The reaction mass was stirred for 2 hours and filtered. To the wet solid was added diluted hydrochloric acid (IN, 800 ml) and stirred for 1 hour, filtered. To the wet solid was added acetone (500 ml) and heated to reflux, and maintained for 30 minutes. The suspension was cooled to room temperature and stirred for 1 hour 30 minutes. The separated solid was filtered and dried at 55 to 60°C for 2 hours to obtain 220 gm of raloxifene hydrochloride.

  • 3
  • [ 63675-74-1 ]
  • [ 84449-80-9 ]
  • [2-(4-hydroxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)-ethoxy]phenyl]methanone hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; thionyl chloride;aluminium trichloride; In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water; chlorobenzene; EXAMPLE 19 6-Methoxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride A mixture of 9 g. of 4-(2-piperidinoethoxy)benzoic acid, hydrochloride, 100 ml. of chlorobenzene, 15 ml. of thionyl chloride and 5 drops of dimethylformamide was stirred at 75°-79° C. for 2 hours, to prepare the corresponding acid chloride. Excess thionyl chloride and part of the chlorobenzene was removed by distillation under vacuum to a maximum pot temperature of 85° C. Fifty ml. of additional chlorobenzene was added, and the distillation of 85° C. was repeated. The residue was then dissolved in 100 ml. of dichloromethane, and to it was added 8.1 g. of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene, 50 ml. of additional dichloromethane and 30 g. of aluminum chloride. The mixture ws stirred at 27°-29° C. for 90 minutes, and was then cooled. To the mixture was added 108 ml. of tetrahydrofuran, followed by 30 ml. of 20percent aqueous hydrochloric acid and 108 ml. of water. The water phase was then removed, and was extracted with 50 ml. of dichloromethane. The organic layers were combined, and extracted with 90 ml. of water. The organic portion was then dried over sodium sulfate, and evaporated to a solid under vacuum. About 31 g. of wet crude product was obtained. The crude product was slurried in 200 ml. of hot chlorobenzene, and the slurry was cooled in an ice bath and filtered at 5° C. The solids were washed with 30 ml. of chlorobenzene, and dried under vacuum to obtain 10.6 g. of the desired product. About 1.8 g. of additional product was obtained by chromatography of the filtrate on silica gel, eluding with methanol. The melting point of the main product was 216° C. dec. Its identity was confirmed by 90 mHz nmr in CDCl3, which showed the following characteristic features. delta1.6 (m, 2H, N(CH2 CH2)2 CH2); 2.0 (m, 4H, N(CH2 CH2)2); 3.1 (m, 4H, N(CH2 CH2)2); 3.3 (m, 2H, CH2 N(CH2)5); 3.7 and 3.9 (s, 3H, OCH3); 4.5 (n, 2H, OCH2) 6.7-7.8 (m, 11H, aromatic).
  • 4
  • [ 79-37-8 ]
  • [ 63675-74-1 ]
  • [ 84449-80-9 ]
  • [ 107-06-2 ]
  • [6-HYDROXY-2-(4-HYDROXYPHENYL)BENZO[B]THIEN-3-YL][4-[2-(1-PIPERIDINYL)ETHOXY]PHENYL]METHANE HYDROCHLORIDE [ No CAS ]
YieldReaction ConditionsOperation in experiment
With boron trichloride; In N-methyl-acetamide; methanol; dichloromethane; Example 4 Preparation of [6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzyl]benzo[b]thiophene hydrochloride] A solution of 4-(2-piperidinoethoxy) benzoic acid hydrochloride (30.01 g) and dimethylformamide (2 mL) in methylene chloride (500 mL) is treated with oxalyl chloride (10.5 mL) over a 30-35 minute period. After stirring for about 18 hours, the reaction is assayed for completion by HPLC analysis. Additional oxalyl chloride may be added to the reaction if the starting carboxylic acid is present. Upon completion, the reaction solution is evaporated to dryness in vacuo. The residue was dissolved in methylene chloride (200 mL), and the resulting solution evaporated to dryness. The dissolution/evaporation procedure is repeated and 6-methoxy-2-(4-methoxyphenyl) benzo[b]thiophene (25.4 g), and 1,2-dichloroethane (450 mL) is added and the reaction is cooled to 0°C. Boron trichloride gas is condensed into a cold graduated cylinder (24.4 mL), and added to the cold mixture described above. After 8 hours at 0°C, the reaction mixture is treated with additional boron trichloride gas (24.4 mL). The resulting solution is heated to 35°C. After 16 hours the reaction is complete. Methanol (250 mL) is added to the reaction mixture over about 20 minutes, causing the methanol to reflux. The resulting slurry is stirred at 25°C. After 1 hour, the crystalline prouduct was filtered, washed with cold methanol (64 mL), and dried at 40°C in vacuo to give the title compound. m.p. 225°C. HPLC.
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