Dimethylformamide → 5-Chloro-2-nitrobenzoyl chloride

HRID 1755628Notes

Reaction equation

HRID 1755628 reaction equation
S(Cl)([Cl:3])=O.CN(C)C=O.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([N+:20]([O-:22])=[O:21])=[C:15]([CH:19]=1)[C:16](O)=[O:17]>C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([N+:20]([O-:22])=[O:21])=[C:15]([CH:19]=1)[C:16]([Cl:3])=[O:17]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 172865-Chloro-2-nitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 27236855-Chloro-2-nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of thionyl chloride (7.25 mL, 99.5 mmol) and N,N-dimethylformamide is added to a mixture of 5-chloro-2-nitrobenzoic acid in toluene. The reaction mixture is heated to and held at 80° C. for 16 hours, cooled to room temperature, concentrated in vacuo, diluted with toluene, concentrated in vacuo and diluted with toluene to obtain the title product as a 1 molar solution in toluene.

Workup

  1. temperatureThe reaction mixture is heated to and
  2. concentrationconcentrated in vacuo
  3. additiondiluted with toluene
  4. concentrationconcentrated in vacuo
  5. additiondiluted with toluene

Sources & evidence

ORD record
ord-b3dadfffeb904afe955d16b54c9e8c2d
Source dataset
uspto-grants-1995_08
Patent number
US05438035

Reaction notes

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