Thionyl Chloride → 4-Chlorothiophene-2-carbonyl chloride

HRID 566205Notes

Reaction equation

HRID 566205 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=O)[S:5][CH:6]=1.S(Cl)([Cl:12])=O>>[Cl: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 Chloride2×HCID 122906954-Chlorothiophene-2-carboxylic acid

Product 1

HCID 158962794-Chlorothiophene-2-carbonyl chloride

Procedure

1.63 g (10.0 mmoles) of 4-chloro-2-thiophenecarboxylic acid (prepared according to Iriarte, J., et al., J. Het. Chem. 13:393 (1976)) was dissolved in 10 ml of thionyl chloride and heated to reflux. After refluxing for 1.5 hours excess thionyl chloride was evaporated, leaving 1.88 g of crude 4-chloro-2-thiophenecarbonyl chloride as a dark brown oil. This acid chloride was dissolved in 10 ml of N,N-dimethylformamide and slowly added to a cooled (ice-water) 40 ml N,N-dimethylformamide solution of 1.75 g (8.33 mmoles) 5-chloro-2-oxindole-1-carboxamide and 3.05 g (25.0 mmoles) of 4-(N,N-dimethylamino)pyridine. The reaction was complete in 1 hour. The mixture was poured into 100 ml of 1N hydrochloric acid causing a precipitate to form. The crude solid was filtered, dried and recrystallized to give 1.89 g (5.3 mmoles, 64% yield) of title compound as yellow needles, m.p. 212-214° C. (2-butanone).

Workup

  1. temperatureheated to reflux
  2. customwas evaporated

Sources & evidence

ORD record
ord-335f38585c7a45cf8b75e8a3abc2f3ca
Source dataset
uspto-grants-2001_01
Patent number
US06174883B1

Reaction notes

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