Aniline → 2-Oxo-N-phenyl-2,3-dihydro-1-benzothiophene-3-carboxamide

HRID 434356Notes

Reaction equation

HRID 434356 reaction equation
[O:1]=[C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[CH:3]1[C:11]([O:13]CC)=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C(C)=CC=CC=1>[C:17]1([NH:16][C:11]([CH:3]2[C:2](=[O:1])[S:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]2=3)=[O:13])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 20493680Ethyl 2-oxo-2,3-dihydro-1-benzothiophene-3-carboxylate

Product 1

HCID 127993852-Oxo-N-phenyl-2,3-dihydro-1-benzothiophene-3-carboxamide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

470 mg (2.11 mmols) of ethyl 2-oxo-2,3-dihydro-3-benzo[b]thiophene-carboxylate and 206 mg (2.22 mmols) of aniline in 3 ml of xylene are boiled under reflux for 5 hours. After cooling, the product is precipitated by adding hexane (3 ml). After further dilution with 5 ml of ether and stirring, crystalline N-phenyl-2-oxo-2,3-dihydro-3-benzo[b]thiophene-carboxamide with a melting point of 140°-142° is obtained and filtered off.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter cooling
  3. customthe product is precipitated
  4. additionby adding hexane (3 ml)

Sources & evidence

ORD record
ord-46c3565867e84a0e99e779d1a4c3b575
Source dataset
uspto-grants-1983_08
Patent number
US04396621

Reaction notes

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