Hydrochloric Acid → 5-Acetylthiophene-3-carboxamide

HRID 1447418Notes

Reaction equation

HRID 1447418 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[S:5]1[CH:9]=[CH:8][C:7]([C:10]([NH2:12])=[O:11])=[CH:6]1.Cl.[Cl-].[Na+].[C:16](Cl)(=[O:18])[CH3:17]>>[C:16]([C:9]1[S:5][CH:6]=[C:7]([C:10]([NH2:12])=[O:11])[CH:8]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 11205757Thiophene-3-carboxamide

Product 1

HCID 205509375-Acetylthiophene-3-carboxamide

Procedure

A solution of aluminium chloride (66.5 g) in acetyl chloride (200 ml) was stirred at room temperature for 1 h. Thiophene-3-carboxamide (12.7 g) was added in one aliquot and the resulting pale yellow solution stirred at room temperature for 4 h before being added cautiously to ice (1 kg) and dilute hydrochloric acid (400 ml). The resulting solution was saturated with sodium chloride and extracted with butanone (6×500 ml) and then ethyl acetate (6×500 ml). The combined organic extracts were evaporated to small volume, diluted with ethyl acetate (1000 ml) and washed thoroughly with sodium carbonate solution (6×100 ml) and water (100 ml) and then dried and evaporated to small volume to deposit the title compound as a white crystalline solid (14.0 g) m.p. 156°-157° which recrystallised from ethyl acetate, m.p. 156°-158°.

Workup

  1. extractionextracted with butanone (6×500 ml)
  2. customThe combined organic extracts were evaporated to small volume
  3. additiondiluted with ethyl acetate (1000 ml)
  4. washwashed thoroughly with sodium carbonate solution (6×100 ml) and water (100 ml)
  5. customdried
  6. customevaporated to small volume
  7. customrecrystallised from ethyl acetate, m.p. 156°-158°

Sources & evidence

ORD record
ord-1f1398f619954798ad9cf2a6cc9b7da4
Source dataset
uspto-grants-1982_02
Patent number
US04316907

Reaction notes

Loading…