Thionyl Chloride → 4-Bromo-2-Thiophenecarbonyl Chloride

HRID 345953

Reaction equation

HRID 345953 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=O)[S:5][CH:6]=1.S(Cl)([Cl:12])=O>>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([Cl:12])=[O:9])[S:5][CH:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 6104094-Bromo-2-thiophenecarboxylic Acid

Product 1

HCID 27954834-Bromo-2-Thiophenecarbonyl Chloride

Procedure

According to the procedure of Preparation A, 2.48 g (12.0 mmoles) of 4-bromo-2-thiophenecarboxylic acid (prepared according to Lawesson, S. O., Arkiv. for Kemi. 11:317 (1957)) and 10 ml of thionyl chloride were combined and heated. The reaction gave 2.99 g of 4-bromo-2-thiophenecarbonyl chloride as a dark oil. The acid chloride, 2.11 g (10.0 mmoles) of 5-chloro-2,3-dihydro-2-oxo-1H-indole-1-carboxamide and 3.67 g (30.0 mmoles) of 4-(N,N-dimethylamino)pyridine were reacted in N,N-dimethylformamide to give 4.03 g of a crude orange solid. Recrystallization gave 2.67 g (6.68 mmoles, 66.8% yield) of title compound as a yellow crystalline solid, m.p. 217°-219° C. (dec.) (2-butanone).

Workup

  1. customprepared
  2. temperatureheated

Sources & evidence

ORD record
ord-3d4a37c19f174497bf81c42705289de9
Source dataset
uspto-grants-1991_10
Patent number
US05059693

Linked notes

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