Oxalyl chloride → HCID 89536828, compound

HRID 1774102Notes

Reaction equation

[Cl:1][C:2]1[C:10]([S:11][CH3:12])=[CH:9][C:8]([CH3:13])=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:14][C:15]1[N:19]([CH3:20])[N:18]=[N:17][N:16]=1.C(Cl)(=O)C(Cl)=O>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Cl:1][C:2]1[C:10]([S:11][CH3:12])=[CH:9][C:8]([CH3:13])=[CH:7][C:3]=1[C:4]([NH:14][C:15]1[N:19]([CH3:20])[N:18]=[N:17][N:16]=1)=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

500 mg (2.31 mmol) of 2-chloro-5-methyl-3-(methylthio)benzoic acid and 320 mg (3.23 mmol) of 5-amino-1-methyltetrazole and a catalytic amount of 4-(dimethylamino)pyridine were dissolved in 10 ml of pyridine. 410 mg (3.23 mmol) of oxalyl chloride were then carefully added dropwise. After ten minutes, the mixture was stirred at 80° C. for 4 h. To bring the reaction to completion, another 137 mg (1.08 mmol) of oxalyl chloride were added at RT and the mixture was stirred at 80° C. for another 4 h. For work-up, the contents were cooled to RT and freed of the solvent on a rotary evaporator, and the residue was dissolved in dichloromethane. The solution was washed with saturated aqueous sodium bicarbonate solution and the organic phase was then freed of the solvent. The residue was purified chromatographically, giving 495 mg of 2-chloro-5-methyl-3-methylthio-N-(1-methyltetrazol-5-yl)benzamide.

Workup

waitAfter ten minutes
customthe reaction to completion
stirringthe mixture was stirred at 80° C. for another 4 h
temperatureFor work-up, the contents were cooled to RT
customfreed of the solvent on a rotary evaporator
dissolutionthe residue was dissolved in dichloromethane
washThe solution was washed with saturated aqueous sodium bicarbonate solution
customThe residue was purified chromatographically

Sources & evidence

ORD record: ord-1352ca8aaf6f42f799801ba0c98e31f0
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09259001B2

Reaction notes

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