Dimethylformamide → 3-Cyanobenzoyl chloride

HRID 1954188Notes

Reaction equation

HRID 1954188 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7])#[N:2].S(Cl)([Cl:14])=O.CN(C)C=O>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([Cl:14])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 158753-Cyanobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 3084833-Cyanobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In 10 ml of toluene, 576 mg of 3-cyanobenzoic acid were suspended, followed by the addition of 699 mg of thionyl chloride and 0.5 ml of N,N-dimethylformamide. The resulting mixture was stirred under heating at 80° C. for 5 hours. After cooling, the solvent was distilled off from the reaction mixture under reduced pressure. To the residue, n-hexane was added. The solvent was then distilled off, whereby 3-cyanobenzoyl chloride was obtained.

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled off from the reaction mixture under reduced pressure
  3. additionTo the residue, n-hexane was added
  4. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-884414b970814fbcb7ef5f28a85c4717
Source dataset
uspto-grants-2000_09
Patent number
US06121301

Reaction notes

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