Dimethylformamide → 3-Cyanobenzoyl chloride

HRID 1954190Notes

Reaction equation

HRID 1954190 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 1 liter of toluene, 200 g of 3-cyanobenzoic acid were suspended, followed by the addition of 128 ml of thionyl chloride and 1 ml of N,N-dimethylformamide. The resulting mixture was stirred under heating at 80° C. for 5 hours. After cooling of the reaction mixture, the solvent was distilled off under reduced pressure. To the residue, n-hexane was added. By distilling off the solvent under reduced pressure, 3-cyanobenzoyl chloride was obtained. The resulting 3-cyanobenzoyl chloride was dissolved in 3 liters of dried 1,2-dichloroethane, followed by the addition of 200 g of 2-amino-4-methoxycarbonyl-1,3-thiazole. The resulting mixture was heated under reflux for 5 hours. The reaction mixture was cooled. Crystals so precipitated were collected by filtration and then washed with water, whereby 289 g of 2-[N-(3-cyanobenzoyl)amino]-4-methoxycarbonyl-1,3-thiazole.hydrochloride were obtained. Yield: 80%.

Workup

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

Sources & evidence

ORD record
ord-838908a5e1f94c15a90adf3de9098d19
Source dataset
uspto-grants-2000_09
Patent number
US06121301

Reaction notes

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