Water → N-phenyl-1-benzothiophene-2-carboxamide

HRID 5337Notes

Reaction equation

HRID 5337 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10](Cl)=[O:11].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C1(C)C=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 142384Benzo[b]thiophene-2-carbonyl Chloride

Product 1

HCID 237071N-phenyl-1-benzothiophene-2-carboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To 8 g (0.0407 mol) of benzothiophene-2-carboxylic acid chloride in 150 ml of toluene there are added with stirring at room temperature 7.6 g (0.0814 mol) of anilin, then, when the addition is complete, the mixture is stirred for 5 hours at 50° C., the reaction mixture is then poured into water, and precipitate which has settled out is filtered off with suction, washed twice with water and dried. 7.9 g (77% of theory) of benzothiophene-2-carboxanilide of melting point 188° C. are obtained. ##STR10##

Workup

  1. additionwhen the addition
  2. filtrationhas settled out is filtered off with suction
  3. washwashed twice with water
  4. customdried

Sources & evidence

ORD record
ord-0d244421dc454fa580394fccb09e3665
Source dataset
uspto-grants-1993_09
Patent number
US05244893

Reaction notes

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