2-amino-N-phenylacetamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.82 Grams (4.13 millimoles) of 2-aminoacetanilide hydrochloride, 0.77 g (4.13 millimoles) of 2-aminoacetanilide (free base) were dissolved in 1.4 milliliters of hot methanol. To this solution was added 0.76 milliliters (0.67 g, 4.13 millimoles) of triethyl orthoacetate. The mixture was heated gently for five minutes. The reaction mixture was cooled and the reaction product precipitated by addition of diethyl ether. The supernatant liquid was decanted, and the precipitate was triturated with ether and collected on a filter. The product was recrystallized from ethanol, and dried to yield about 300 milligrams of N,N'-bis[phenylcarbamylmethyl]acetamidine hydrochloride. The mixture was heated gently for five minutes The reaction mixture was cooled the reaction product precipitated by addition of diethyl ether The supernatant liquid was decanted the precipitate was triturated with ether collected on a filter The product was recrystallized from ethanol dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 179 mg (0.49 mmol) of mono(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, 245mg (1.63 mmol) of 2-amino-N-phenylacetamide, 129 mg (0.67 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 11 mg (0.09 mmol) of 4-dimethylaminopyridine were stirred in 10 ml of dichloromethane at room temperature overnight. Ethyl acetate was added to the reaction mixture, and the product was washed with 1 N hydrochloric acid and then with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (chloroform/methanol=100/1) to obtain the title compound. the product was washed with 1 N hydrochloric acid The organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by the silica gel chromatography (chloroform/methanol=100/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 40 ml of dichloromethane and 20 ml of trifluoroacetic acid were added to 687 mg (2.74 mmol) of t-butyl phenylcarbamoylmethylcarbamate, and they were stirred at room temperature for 3 hours. Dichloromethane and trifluoroacetic acid were evaporated under reduced pressure. A saturated aqueous sodium hydrogencarbonate solution was added to the residue. After the extraction with ethyl acetate and then with dichloromethane, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain the title compound. Dichloromethane and trifluoroacetic acid were evaporated under reduced pressure A saturated aqueous sodium hydrogencarbonate solution was added to the residue After the extraction with ethyl acetate with dichloromethane, the organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The starting material is prepared as follows: The mixture of 38.8 g 4-chloro-5-chlorosulfonyl-3-nitrobenzoic acid, 39.9 g of 2-aminoacetanilide and 150 ml of dimethylformamide is stirred for 21/2 hours at room temperature. It is poured into 1.7 lt of water and 20 ml of concentrated hydrochloric acid while stirring, the precipitate formed is filtered off and washed with water. It is dissolved in 600 ml of hot ethanol, 900 ml of hot water are added, the mixture filtered and the filtrate left in the cold, to yield the 4-chloro-5-(2-acetamidophenylsulfamoyl)-3-nitrobenzoic acid melting at 225°-227° with decomposition. [In the analogous manner the 5-(4-acetamidophenylsulfamoyl)-isomer is prepared, m.p. 245°-246° (dec.).] The starting material is prepared while stirring the precipitate formed is filtered off washed with water It is dissolved in 600 ml of hot ethanol 900 ml of hot water are added the mixture filtered the filtrate left in the cold,

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The starting material is prepared as follows: The mixture of 38.8 g 4-chloro-5-chlorosulfonyl-3-nitrobenzoic acid, 39.9 g of 2-aminoacetanilide and 150 ml of dimethylformamide is stirred for 2 1/2 hours at room temperature. It is poured into 1.7 1t of water and 20 ml of concentrated hydrochloric acid while stirring, the precipitate formed is filtered off and washed with water. It is dissolved in 600 ml of hot ethanol, 900 ml of hot water are added, the mixture filtered and the filtrate left in the cold, to yield the 4-chloro-5-(2-acetamidophenylsulfamoyl)-3-nitrobenzoic acid melting at 225°-227° with decomposition. The starting material is prepared while stirring the precipitate formed is filtered off washed with water It is dissolved in 600 ml of hot ethanol 900 ml of hot water are added the mixture filtered the filtrate left in the cold,