(Z)-1-(3-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one

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

Procedure: A mixture of 50.0 g of 3'-chloro-3-dimethylaminoacrylophenone, 25.0 g of 3-aminopyrazole-4-carbonitrile and 500 ml of glacial acetic acid was heated at reflux for 2 hours. The mixture went into solution upon heating and a precipitate formed after one hour of refluxing. The reaction mixture was filtered and the crystals collected were triturated with saturated aqueous sodium bicarbonate, filtered and washed with water and then dried to give 49.0 g of the product of the example as colorless crystals, mp 238°-240° C. was heated at reflux for 2 hours upon heating a precipitate formed after one hour of refluxing The reaction mixture was filtered the crystals collected were triturated with saturated aqueous sodium bicarbonate filtered washed with water dried

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

Procedure: A mixture of 13.9 g of 4-amino-5-imidazolecarboxamide hydrochloride, 24.0 g of 3'-chloro-3-dimethylaminoacrylophenone (U.S. Pat. No. 4,209,621, Ex. 50) and 200 ml glacial acetic acid was heated at reflux for 5 hours. The liquid was evaporated in vacuo to give a yellow solid. The excess acid was neutralized with saturated sodium bicarbonate solution and this mixture was filtered and the solid was washed with water and then was dried. Recrystallization from ethanol-methanol gave 10.2 g of the desired product as yellow crystals, mp 252°-254° C. at reflux for 5 hours The liquid was evaporated in vacuo to give a yellow solid this mixture was filtered the solid was washed with water was dried Recrystallization from ethanol-methanol

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

Procedure: A mixture of 13.9 g of 4-amino-5-imidazolecarboxamide hydrochloride, 24.0 g of 3'-chloro-3-dimethylaminoacrylophenone (U.S. Pat. No. 4,209,621, Ex. 50) and 200 ml glacial acetic acid was heated at reflux for 5 hours. The liquid was evaporated in vacuo to give a yellow solid. The excess acid was neutralized with saturated sodium bicarbonate solution and this mixture was filtered and the solid was washed with water and then was dried. Recrystallization from ethanol-methanol gave 10.2 g of the desired product as yellow crystals, mp 252°-254° C. at reflux for 5 hours The liquid was evaporated in vacuo to give a yellow solid this mixture was filtered the solid was washed with water was dried Recrystallization from ethanol-methanol

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

Procedure: A mixture of 50.0 g of 3'-chloro-3-dimethylaminoacrylophenone, 25.0 g of 3-aminopyrazole-4-carbonitrile and 500 ml of glacial acetic acid was heated at reflux for 2 hours. The mixture went into solution upon heating and a precipitate formed after one hour of refluxing. The reaction mixture was filtered and the crystals collected were triturated with saturated aqueous sodium bicarbonate, filtered and washed with water and then dried to give 49.0 g of the product of the example as colorless crystals, mp 238°-240° C. was heated at reflux for 2 hours upon heating a precipitate formed after one hour of refluxing The reaction mixture was filtered the crystals collected were triturated with saturated aqueous sodium bicarbonate filtered washed with water dried

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

Procedure: A mixture of 13.9 g of 4-amino-5-imidazolecarboxamide hydrochloride, 24.0 g of 3'-chloro-3-dimethylaminoacrylophenone (U.S. Pat. No. 4,209,621, Ex. 50) and 200 ml of glacial acetic acid was heated at reflux for 5 hours. The liquid was evaporated in vacuo to give a yellow solid. The excess acid was neutralized with saturated sodium bicarbonate solution and this mixture was filtered and the solid was washed with water and then was dried. Recrystallization from ethanol-methanol gave 10.2 g of the desired product as yellow crystals, mp 252°-254° C. at reflux for 5 hours The liquid was evaporated in vacuo to give a yellow solid this mixture was filtered the solid was washed with water was dried Recrystallization from ethanol-methanol

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

Procedure: A mixture of 13.9 g of 4-amino-5-imidazolecarboxamide hydrochloride, 24.0 g of 3'-chloro-3-dimethylaminoacrylophenone (U.S. Pat. No. 4,209,621, Ex. 50) and 200 ml glacial acetic acid was heated at reflux for 5 hours. The liquid was evaporated in vacuo to give a yellow solid. The excess acid was neutralized with saturated sodium bicarbonate solution and this mixture was filtered and the solid was washed with water and then was dried. Recrystallization from ethanol-methanol gave 10.2 g of the desired product as yellow crystals, mp 252°-254° C. at reflux for 5 hours The liquid was evaporated in vacuo to give a yellow solid this mixture was filtered the solid was washed with water was dried Recrystallization from ethanol-methanol

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

Procedure: A mixture of 50.0 g of 3'-chloro-3-dimethylaminoacrylophenone, 25.0 g of 3-aminopyrazole-4-carbonitrile and 500 ml of glacial acetic acid was heated at reflux for 2 hours. The mixture went into solution upon heating and a precipitate formed after one hour of refluxing. The reaction mixture was filtered and the crystals collected were triturated with saturated aqueous sodium bicarbonate, filtered and washed with water and then dried to give 49.0 g of the product of the example as colorless crystals, mp 238°-240° C. was heated at reflux for 2 hours upon heating a precipitate formed after one hour of refluxing The reaction mixture was filtered the crystals collected were triturated with saturated aqueous sodium bicarbonate filtered washed with water dried