Dimethylformamide → 2,3,5-Trichlorobenzoyl chloride

HRID 745911Notes

Reaction equation

HRID 745911 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C)C=O.S(Cl)([Cl:20])=O>>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([Cl:20])=[O:5]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 661212,3,5-Trichlorobenzoic acid

Product 1

HCID 130111162,3,5-Trichlorobenzoyl chloride

Procedure

A mixture of 2,3,5-trichlorobenzoic acid (90 g, 0.4M) and dimethylformamide (1 ml) in thionyl chloride (200 ml) was heated to reflux for 2 hours. The cooled solution was evaporated down in vacuo and the residue distilled under nitrogen. Yield 89.2 g (90%), b.p. 158°-160° C. at the pressure of 30 mm of mercury.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThe cooled solution was evaporated down in vacuo
  4. distillationthe residue distilled under nitrogen

Sources & evidence

ORD record
ord-ed6bd64a70a54a7fb79c2f1381dae1aa
Source dataset
uspto-grants-1986_07
Patent number
US04602017

Reaction notes

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