Thionyl Chloride → 2,6-Dichloro-4-nitrobenzoyl chloride

HRID 746038Notes

Reaction equation

HRID 746038 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([Cl:14])[C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:17])=O>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([Cl:14])[C:3]=1[C:4]([Cl:17])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 225719382,6-Dichloro-4-nitrobenzoic acid

Product 1

HCID 225716812,6-Dichloro-4-nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,6-dichloro-4-nitrobenzoic acid (1.53 g, 6.5 mmol), thionyl chloride (1.0 cm3, 13.7 mmol) and N,N-dimethylformamide (0.1 cm3) were heated under reflux for 1.5 h. The mixture was evaporated under reduced pressure to an oil which was purified by evaporative distillation yielding 2,6-dichloro-4-nitrobenzoyl chloride as a pale yellow oil (1.37 g, bp 140° C. at 0.2mm Hg) which solidified with cooling. (mp 63°-5° C.).

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 1.5 h
  3. customThe mixture was evaporated under reduced pressure to an oil which
  4. distillationwas purified by evaporative distillation

Sources & evidence

ORD record
ord-3cbe8e97f2e34cfca5dbc15b42556b78
Source dataset
uspto-grants-1986_07
Patent number
US04602041

Reaction notes

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