Ethyl cyanoacetate → HCID 131718324, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 14.5 grams (50 mmol) of 2-(4-sulfoanilino)acetophenone, 45.2 grams (0.4 mol) of ethyl cyanoacetate and 12.2 grams (0.2 mol) of ammonium acetate in a reaction flask fitted with distillation head was stirred and placed in an oil bath pre-heated to 130° C. At an internal temperature of 60° C. the reaction mixture became easily stirrable. Distillate began to collect at 95° C. and the reaction was brought to an internal temperature of 115° C. After 25 minutes the product mixture had become a thick slurry. The product mixture was then cooled, diluted with 100 mL of ethanol and stirred. The tan-yellow product was collected by filtration and washed with ethanol, acetone and ligroin to give a crude weight of product of 10.1 grams. The product was recrystallized from glacial acetic acid to give 9.35 grams (26 mmol, 52% yield) of product as a yellow powder, m. p.=275°-300° C. (decomposes). Elemental Analysis: Calculated: C=57.13, H=4.23, N =11.76, S=8.97; Found: C=57.07, H=4.31, N=11.66, S=8.40.

Provenance & Evidence