* 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.
With triethylamine;copper diacetate; In dichloromethane;
Example 28 4-Methoxy-3-phenylamino-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (1.5 g, 6.2 mmol), triphenylbismuth (2.9 g, 6.6 mmol), copper(II) acetate (1.13 g, 6.2 mmol), and triethylamine (0.62 g, 6.2 mmol) to give a solid which was recrystallized from ethanol then subjected to chromatography on a column of silica gel in dichloromethane to afford the product (0.8 g); m.p. 194-195 C. after an additional recrystallization from ethyl alcohol. Calculated for C20H18N2O2: C, 75.45; H, 5.70; N, 8.80. Found: C, 74.66; H, 5.43; N, 8.67.
3-(2-methoxy-phenylamino)-4-methoxy-N-phenyl-benzamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine;copper diacetate;
Example 29 3-(2-Methoxy-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (0.8 g, 3.2 mmol), tris(2-methoxyphenyl)bismuthine (1.8 g, 3.4 mmol), copper(II) acetate (0.6 g, 3.4 mmol), and triethylamine (0.34 g, 3.4 mmol) to afford the product (0.9 g); m.p. 155-156 C. after chromatography on a column of silica gel in chloroform followed by recrystallization from ethanol.
3-(3-chlorophenylamino)-4-methoxy-N-phenylbenzamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine;copper diacetate; In chloroform; ethyl acetate;
Example 31 3-(3-Chloro-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (1.5 g, 6.2 mmol), tris(3-chlorophenyl)bismuthine (3.5 g, 6.4 mmol), copper(II) acetate (1.16 g, 6.4 mmol), and triethylamine (0.65 g, 6.4 mmol) to give a solid which was purified by chromatography on a column of silica gel in chloroform/ethyl acetate 99:1 to afford the product (1.8 g); m.p. 168-170 C. after recrystallization from ethanol. Calculated for C20H17ClN2O2: C, 68.09; H, 4.86; N, 7.94. Found: C, 67.91; H, 4.71; N, 7.80.
3-(3,5-dimethyl-phenylamino)-4-methoxy-N-phenyl-benzamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine;copper diacetate;
Example 36 3-(3,5-Dimethyl-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (1.5 g, 6.3 mmol), tris(3,5-dimethylphenyl)-bismuthine (3.3 g, 6.3 mmol), copper(II) acetate (1.15 g, 6.3 mmol), and triethylamine (0.64 g, 6.3 mmol) to afford the product (1.1 g); m.p. 198-199 C. after recrystallization from a mixture of dichloromethane and ethyl acetate 10:1. Calculated for C22H22N2O2.0.5CH2Cl2: C, 75.52; H, 6.35; N, 7.99. Found: C, 75.56; H, 6.32; N, 7.92.
With hydrogenchloride; sodium nitrite; In water; at 0℃; for 1h;
(EXAMPLE 7); (Preparation of Solution A); In 75 g of ultra pure water is dispersed 5 g (0.021 mol) of <strong>[120-35-4]3-amino-4-methoxybenzanilide</strong>, and the resultant dispersion is cooled to 0C with stirring in an ice bath to which methanol has been added. Further, 6 g (0.058 mol) of 35% hydrochloric acid is added, and the resultant mixture is stirred for 10 minutes. Thereafter, 1.45 g (0.021 mol) of sodium nitrite is dissolved in 2 ml of ultra pure water, and the solution is then added to the mixture. After stirring the mixture for 60 minutes, 0.2 g (0.002 mol) of sulfamic acid is added to eliminate nitrous acid, thereby preparing a diazonium salt solution.
With hydrogenchloride; sodium nitrite; at 5℃;Industry scale;Product distribution / selectivity;
3-Amino-4-methoxybenzanilide was diazotized in a manner known per se in the art by using a 3.5-fold molar amount of hydrochloric acid and an equimolar amount of sodium nitrite, followed by the addition of sodium acetate to prepare a 0.025 mole/L diazo solution of pH 4.0 (40 L, solution temperature: 5 C.). On the side, N-(4-chloro-2,5-dimethoxyphenyl)-3-hydroxy-2-napthaleneca rboxamide (naphthol AS-LC) (362 parts) was dissolved in an aqueous solution, which contained sodium hydroxide (100 parts), to prepare a 0.126 mole/L grounding solution (8 L, solution temperature: 20 C.); 3-Amino-4-methoxybenzanilide was diazotized in a manner known per se in the art by using a 3.5-fold molar amount of hydrochloric acid and an equimolar amount of sodium nitrite, followed by the addition of sodium acetate to prepare a 0.05 mole/L diazo solution of pH 4.0 (20 L, solution temperature: 5 C.). As a grounding solution, on the other hand, the grounding solution (8L, solution temperature: 20 C.) prepared in Example 3 was used. As illustrated in FIG. 3, the diazo solution was next caused to flow as a first fluid I at a flow rate of 5 L/min by the feed pump d from the first feed tank 2 into the ejector 1 through the first flow path a. Owing to depressurization occurred in the ejector 1, the grounding solution was drawn as a second fluid II at a flow rate of 1 L/min (adjusted by the first flow control means e) from the second feed tank 3 through the second flow path b into the ejector 1 maintained at 20 C. by the temperature control means g, and through a coupling reaction, a naphthol AS pigment (PR146) was yielded.
Open the exhaust butterfly valve,2000KG water was injected into the diazo reaction tank,29.3 parts of hydrochloric acid was added and the agitator was started.14.6 parts of red-based KD were added from the manhole,Stirred for 10 minutes,Cooled to 0 C or lower with ice,A solution of 4.6 parts of sodium nitrite, which was completely dissolved, was quickly added,A minute later with potassium iodide test paper was purple.Maintaining the temperature of the diazo component below 5 C,After 1.5 hours, 0.5 parts of sulfamic acid (preliminarily dissolved) was added,Two minutes after potassium iodide test strip diazonium salt solution is colorless,Turn off the blender butterfly valve.
A process according to claim 1 wherein the diazotizable amine is selected from the group consisting of 2,4- and 2,5-dichloraniline, ... 2-methoxy-5-methyl-4-aminobenzene sulphonic acid methyl amide, 2,5-dimethoxy-4-aminobenzoic sulphonic acid anilide, 2-methoxy-5-methyl-4-benzoylaminoaniline, 4-ethoxy-3-aminobenzamide, 4-methoxy-3-aminobenzoic acid anilide, 4-methyl-3-aminobenzoic acid-2'4'-dimethylanilide, 4-methyl-3-aminobenzoic acid-4'-chloranilide, 4-chloro-3-aminobenzoic acid-2'-methyl-5'-chloranilide, ...
Representative compounds of formula (1) that may be employed are: ... N'-n-butyl-3-amino-4-methoxybenzenesulfonamide N'-(gamma-methoxypropyl)-3-amino-4-methoxybenzenesulfonamide N'-methyl-3-amino-4-methoxybenzenesulfonamide 3-amino-4-methoxyphenylbenzylsulfone 3-amino-4-methoxybenzanilide 2-amino-1-phenol-4-sulfonanilide 2-amino-4-(methylsulfonyl)phenol 4-amino-3-hydroxy-4'-chlorobenzenesulfonanilide ...
Exemplary amines and diamines useful in the invention are: ... 2-aminobenzoic acid 2-trifluoromethylaniline 3-amino-4-methoxybenzanilide
9
[ 120-35-4 ]
[ 169762-05-4 ]
Yield
Reaction Conditions
Operation in experiment
With hydrogenchloride; trichlorophosphate; In water; N,N-dimethyl-aniline;
Step A Preparation of 3-Amino-4-methoxy-4'-N,N-Di-methylaminobenzophenone STR262 Fifty grams (0.2 mole) of <strong>[120-35-4]3-amino-4-methoxybenzanilide</strong>, 70 g (0.58 mole) N,N-dimethylaniline and 36 g POCl3 were heated on a water bath at 90 C. to 95 C. for 4 to 6 hours. The product was then cautiously poured into a solution of 23 ml of concentrated hydrochloric acid in 250 ml water. The resulting solution was warmed at 80 C. until the initial reddish color disappeared, indicating that the aniline was completely hydrolyzed. A liter of water was added to precipitate the ketone, which was filtered, washed with cold water, and recrystallized from a 2:1 aqueous alcohol solution. Yield: 38 g of slightly yellowish crystals, metling point 82 C.
EXAMPLE 5 3-Amino-4-Methoxybenzanilide According to the procedure of Example 1, substituting 135.5 g. of benzoyl chloride for the acetic anhydride used therein, 2,4-dinitrochlorobenzene was converted to 3-amino-4-methoxybenzanilide, in 79% yield.
3-[3-(4-Chloro-3-trifluoromethylphenyl)-thioureido]-4-methoxy-N-phenyl-benzamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In ethyl acetate;
Example 73 3-[3-(4-Chloro-3-trifluoromethylphenyl)-thioureido]-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 60 using 3-amino-4-methoxy-N-phenyl-benzamide (0.972 g, 4.0 mmol) and 4-chloro-3-(trifluoromethyl)phenyl isothiocyanate (0.961 g, 4.0 mmol). Trituration in hexanes/ethyl acetate (3:2) gave the product (1.91 g); m.p. 172-173 C. Calculated for C23H17Cl2N3O2S: C, 55.06; H, 3.57; N, 8.76. Found: C, 54.88; H, 3.26; N, 8.58.
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