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[ CAS No. 147962-41-2 ] {[proInfo.proName]}

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Chemical Structure| 147962-41-2
Chemical Structure| 147962-41-2
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CAS No. :147962-41-2 MDL No. :MFCD12755184
Formula : C3H10N2O2S Boiling Point : No data available
Linear Structure Formula :- InChI Key :FEYGBGVBTKYFOF-UHFFFAOYSA-N
M.W : 138.19 Pubchem ID :13949558
Synonyms :

Safety of [ 147962-41-2 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 147962-41-2 ]

* 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 [ 147962-41-2 ]

[ 147962-41-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 146533-41-7 ]
  • [ 147962-41-2 ]
  • [ 1393813-42-7 ]
YieldReaction ConditionsOperation in experiment
89% A.ii. N-(5-(4-bromophenyl)-6-chloropyrimidin-4-yl)propane-1-sulfamide:tBuOK (16.0 g; 0.14 mol; 1 eq.) was added to the above prepared cold (5C) solution of Intermediate A.i in DMSO. The resulting suspension was heated to 20C and stirred for 30 mi <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong> (10.7 g; 0.035 mol; 0.25 eq.) was added portionwise and the mixture was heated to 50C for 1 h. Water was added. The pH of the solution was adjusted to 4-5 using 33% aq. HC1. The suspension was cooled to 0C and stirred for 30 mm. It was filtered off, rinsed with a solution of water and MeOH and dried under reduced pressure to yield the title compound as a white solid (12.6 g, 89% yield with respect to S -(4-bromophenyl)-4,6-dichloropyrimidine).
89% A.ii. N- (5 -(4-bromopheny I) -6-chloropyrimidin-4-yl)propane- 1-sulfamide; tBuOK (16.0 g; 0.14 mol; 1 eq.) was added to the above prepared cold (5C) solution of Intermediate A.i in DMSO. The resulting suspension was heated to 20C and stirred for 30 min. <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong> (10.7 g; 0.035 mol; 0.25 eq.) was added portion wise and the mixture was heated to 50C for 1 h. Water was added. The pH of the solution was adjusted to 4-5 using 33% aq. HCl. The suspension was cooled to 0C and stirred for 30 min. It was filtered off, rinsed with a solution of water and MeOH and dried under reduced pressure to yield the title compound as a white solid (12.6 g, 89% yield with respect to <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong>).
With lithium amide; In dimethyl sulfoxide; at 15 - 25℃; for 2h;Inert atmosphere; To a solution of V-propylsulfamide (25.0 gm, 0.180 mol) in dimethylsulfoxide (250.0 ml) was added Lithium amide (7.6 gm, 0.33 mol) under nitrogen atmosphere at 15-25 C, followed by addition of 5-(4-bromophenyl)-4,6- dichloropyrimidine (50.0 gm, 0.164 mol). The reaction mass was stirred for 2 hr. at room temperature and the progress of reaction was monitored by HPLC. After reaction completion this reaction mass was drop wise added to the solution containing Lithium amide (7.6 gm, 0.33 mol) and ethylene glycol (250.0 ml) at 15-25 C under nitrogen atmosphere. After the addition reaction mixture was heated to 105 - 110C, maintained for 18-24 hours and the reaction progress was monitored by HPLC. After completion of reaction, resulting mass was cooled to 25-30 C and 5% w/v citric acid solution (1000.0 ml) was added to the reaction mass. The product was extracted twice with ethyl acetate (1000.0 ml x 2), further organic layer was washed twice with 10% w/v brine solution (500.0 ml x 2). Organic layer was concentrated at 55-60C under reduced pressure to produce A/-5-(4- bromophenyl)-6-(-2-hydroxyethoxy)-4-pyrimidinyl-//-propylsulfamide as a residue. The obtained residue was dissolved in methanol 65-70 C and maintained for 30 min. The resulting solution was gradually cooled to room temperature then cooled to 0-5C and maintained reaction mass at 0-5C for 60-90 min. Obtained solid was filtered, washed with methanol (50.0 ml), suck dried and dried at 55-60C to afford white solid of N-5-(4-bromophenyl)-6-(- 2hydroxyethoxy)-4-pyrimidinyl- N'-propylsulfamide. [Yield = 50.0 gm (70.48 %); Purity (HPLC) = 98.50 %]. (M + H)7z= 433.0. 1H NMR (CDCl3): delta 8.46-8.45 (s, 1 H), 7.65-7.62 (m, 2H), 7.25-7.17 (m, 2H), 6.91 (s, br, 1 H), 5.62-5.69 (t, 1 H), 4.48-4.46 (m, 2H), 3.84- 3.81 (m, 2H), 2.97-2.92 (q, 2H), 2.97-2.92 (t, 1 H), 1.16-1.52 (h, 2H), 0.94- 0.91 (t, 3H). 3C NMR (CDC ): delta 11.31 , 22.07, 44.74, 59.20, 68.32, 104.94, 121.42, 129.84, 131.55, 132.79, 155.91 , 156.38, 166.26.
Potassium tert-butoxide(90 gm, 0.802 mol) was added in to a reaction flask containing a solution of N-Propyl-sulfamide (N-Propyl-sulfamide (82 gm, 0.593 mol) in DMSO (250 ml)) and stirred the reaction mass at room temperature for 30 min to obtain potassium salt of N- propyl sulfamide. <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong> (100 gm, 0.329 mol) was added in to the reaction mass and stirred the contents for 5-6 hrs at 25-30C. DM water (500 ml) was added to the reaction mass a stirred solution. Further 10% citric acid solution (500 ml) was added slowly for an about 1 -2 hrs to obtain solid. The precipitated solid was filtered and washed with DM water (120 ml) and suck dried the material for 30 min. The product was dried under vacuum at 50-55 C for 10-12 hrs to obtain title product. Yield: 137 gm; Purity (By HPLC): 92.0%
With lithium amide; In dimethyl sulfoxide; at 20 - 25℃; for 2h; To a stirred solution of 2.0 kg 5-(4-Bromophenyl)-4,6-dichloropyrimidine (2, 6.57 mol) in 20 dm3 DMSO,0.303 kg lithium amide (13.15 mol) and 1.0 kg N-propylsulfamide(3, 7.23 mol) were added at 20-25 C. The reaction mass was stirred at 20-25 C for 2-6 h (completionof the reaction was monitored by HPLC).

  • 2
  • [ 146533-41-7 ]
  • [ 147962-41-2 ]
  • [ 107-21-1 ]
  • C28H32Br2N8O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1, 8 ml of N, N-dimethylformamide, 100 g (724 mmol) of N-propylsulfamide, 26 g (1083 mmol) of sodium hydride were added to the 1 L three-necked reaction flask, and the mixture was stirred at 10 to 15 C for 30 min, (724 mmol) of 4-bromophenyl-4,6-dichloropyrimidine was stirred at 20-25 C for 8 h and then stirred at 35-40 C for 1 h, cooled to 10-15 C,22.3 g (35.9 mmol) of ethylene glycol was added,And p-toluenesulfonyl chloride (137 g, 71.9 mmol) were added and the temperature was raised to 85-95 C. The reaction was continued for 9 h, cooled to 0-10 C. The solution was crystallized by adding 10 wt% citric acid aqueous solution. The filter cake was washed with purified water neutral,The solid was collected and dried at 40-50 C under vacuum (vacuum ? 0.08 MPa) for 8 h to give 212.5 g of crude impurities and 73.9% yield. 2, to 212.5g impurity crude addition of ethyl acetate 700ml, 75-85 C heating and stirring dissolved, hot filter, the filtrate plus methanol 3000ml crystallization, filtration, filter cake with methanol amount of washing, collecting solid,At 40-50 under reduced pressure (vacuum ? 0.08MPa) dry 8h,A mixture of 1,2-bis [[N- [5- (4-bromophenyl)] - N'-propylsulfonamide-6-oxo] pyrimidinyl] ethyl dithioate was obtained in a yield of 76.5 %.
  • 3
  • [ 146533-41-7 ]
  • [ 147962-41-2 ]
  • [ 1393813-42-7 ]
  • C16H23BrN6O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% A mixture of 1 (100 g, 0.33 mol), K2CO3 (221 g, 1.6 mol), and acetonitrile (1.3 L) washeated to 50C and stirred for 20 min. The solution of 2 (43 g, 0.31 mol) in acetonitrile(200 mL) was added dropwise and maintained at 50C for 10 h. The reaction solvent wasreplaced with toluene (2 L) using a Dean-Stark apparatus. The precipitated solid was filteredand suspended in water (2 L). The pH was adjusted to 7 by using 6 N hydrochloricacid and stirred for 20 min. The resulting precipitate was filtered and dried in the oven at55C for 5 h. The crude product was recrystallized from ethyl acetate to acquire 106 g(85%) of 3 as a white solid, mp 236C-238C. IR (KBr): 3272, 2966, 1593, 1566, 1438.1H NMR (500 MHz, DMSO-d6): d 0.73-0.76 (t, JD6.9, Me); 1.30-1.36 (m, CH2), 2.52-2.56 (m, CH2), 5.68-5.71 (t, JD6.6, NH), 7.12-7.14 (d, 2 H, ArH), 7.50-7.51 (d, 2 H,ArH), 8.04 (s, 1 H, ArH). 13C NMR (125 MHz, DMSO): d 12.41, 21.63, 45.75, 120.26,120.93, 131.50, 133.38, 136.21, 155.26, 156.73, 164.76.
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