Oxalyl chloride → 3-chloro-2-fluoro-N-methoxy-N-methylbenzamide

HRID 1294860Notes

Reaction equation

HRID 1294860 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].Cl.[CH3:13][NH:14][O:15][CH3:16].C(Cl)(=O)C(Cl)=O>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([N:14]([O:15][CH3:16])[CH3:13])=[O:6]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 3029313-Chloro-2-fluorobenzoic acid

Product 1

HCID 114700033-chloro-2-fluoro-N-methoxy-N-methylbenzamideYield 88.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared according to Method A step A from 3-chloro-2-fluorobenzoic acid (3.0 g, 17.2 mmol), N,O-dimethylhydroxylamine hydrochloride (2.34 g, 24 mmol), oxalyl chloride (1.5 mL, 17.2 mmol) and 5 mL of pyridine to give the title compound (3.3 g) as an oil. Used as is in the next prep

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-67f2870a199f461aa0e6d7f48fcb8744
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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