Ethyl cyanoacetate → HCID 131718324, compound

HRID 1974437Notes

Reaction equation

HRID 1974437 reaction equation
[S:1]([C:5]1[CH:20]=[CH:19][C:8]([NH:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)=[CH:7][CH:6]=1)([OH:4])(=[O:3])=[O:2].[C:21]([CH2:23][C:24](OCC)=[O:25])#[N:22].C([O-])(=O)C.[NH4+]>>[NH4+:9].[C:21]([C:23]1[C:24](=[O:25])[N:9]([C:8]2[CH:19]=[CH:20][C:5]([S:1]([OH:4])(=[O:3])=[O:2])=[CH:6][CH:7]=2)[CH2:10][C:11]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[N:22]

Participants

4

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 19101521HCID 19101521, compound

Product 1

HCID 131718324HCID 131718324, compoundYield 104%

Conditions

Temperature
130 °C

Procedure

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.

Workup

  1. customfitted with distillation head
  2. customplaced in an oil bath
  3. customAt an internal temperature of 60° C.
  4. customto collect at 95° C.
  5. customwas brought to an internal temperature of 115° C
  6. temperatureThe product mixture was then cooled
  7. additiondiluted with 100 mL of ethanol
  8. stirringstirred
  9. filtrationThe tan-yellow product was collected by filtration
  10. washwashed with ethanol, acetone and ligroin
  11. customto give a crude weight of product of 10.1 grams
  12. customThe product was recrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-5408040ad2934a55b6cc382cf055b25f
Source dataset
uspto-grants-1994_02
Patent number
US05283165

Reaction notes

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