Ammonia → 5-Acetylthiophene-2-carboxamide

HRID 1447420Notes

Reaction equation

HRID 1447420 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].S(Cl)(Cl)=O.[NH3:16]>C1C=CC=CC=1.O1CCCC1>[C:1]([C:4]1[S:8][C:7]([C:9]([NH2:16])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl Chloride2×HCID 37427275-Acetylthiophene-2-carboxylic acid

Product 1

HCID 189380255-Acetylthiophene-2-carboxamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-acetylthiophene-2-carboxylic acid (5.6 g) and thionyl chloride (5.25 ml) in benzene (70 ml) was refluxed for 3 h; a further portion of thionyl chloride (5.3 ml) was added and reflux continued for 1.5 h. The resulting solution was evaporated to leave a white solid which was dissolved in tetrahydrofuran (70 ml). Aqueous ammonia (s.g. 0.88; 6 ml) was added and the reaction mixture was stirred for 1 h. The white precipitate was washed with water, leaving the title amide (3.43 g) mp 231°-233°. TLC SiO2 (EtOAc) Rf 0.28.

Workup

  1. temperaturewas refluxed for 3 h
  2. temperaturereflux
  3. customThe resulting solution was evaporated
  4. customto leave a white solid which
  5. washThe white precipitate was washed with water

Sources & evidence

ORD record
ord-13edb63ff700400db078e438f416ab66
Source dataset
uspto-grants-1982_02
Patent number
US04316907

Reaction notes

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