3-Cyanobenzoyl chloride → HCID 23296369, compound

HRID 1954191Notes

Reaction equation

HRID 1954191 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([Cl:8])=[O:7])#[N:2].[NH2:12][C:13]1[S:14][CH:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[N:17]=1>ClCCCl>[ClH:8].[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[N:17]=1)=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 3084833-Cyanobenzoyl chlorideHCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylate

Product 1

HCID 23296369HCID 23296369, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperatureThe reaction mixture was cooled
  4. customCrystals so precipitated
  5. filtrationwere collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-d501c9f84fd94bd0bcdff99b85230e45
Source dataset
uspto-grants-2000_09
Patent number
US06121301

Reaction notes

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