Oxalyl chloride → 2,3-difluoro-N-methoxy-N-methylbenzamide

HRID 1294862Notes

Reaction equation

HRID 1294862 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:13][NH:14][O:15][CH3:16].C(Cl)(=O)C(Cl)=O>N1C=CC=CC=1>[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:14]([O:15][CH3:16])[CH3:13])=[O:5]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 3705902,3-Difluorobenzoic acid

Product 1

HCID 626611902,3-difluoro-N-methoxy-N-methylbenzamideYield 93.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared according to Method A step A from 2,3-difluorobenzoic acid (4.0 g, 25 mmol), N,O-dimethylhydroxylamine hydrochloride (3.4 g, 35 mmol), oxalyl chloride (2.2 mL, 25 mmol) and 6 mL of pyridine to give the title compound (4.7 g) as an oil. Used as is in the next preparation.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0d3e1950520446c4a33526cb36d3b4ab
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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