2,6-Difluorobenzamide → Ethyl 2,6-difluorobenzene-1-carboximidate

HRID 637989Notes

Reaction equation

HRID 637989 reaction equation
F[B-](F)(F)F.[CH2:6]([O+](CC)CC)[CH3:7].[F:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:15]=1[C:16]([NH2:18])=[O:17].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:15]=1[C:16](=[NH:18])[O:17][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 874392,6-DifluorobenzamideHCID 516892Sodium BicarbonateHCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 13730259Ethyl 2,6-difluorobenzene-1-carboximidateYield 90.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of triethyloxonium tetrafluoroborate (8.0 g, 0.042M), 2,6-difluorobenzamide (5.62 g, 0.036M) and methylene chloride was stirred at 20° C. for 18 hours, after which an excess of aqueous sodium bicarbonate solution was added. The methylene chloride phase was separated and dried over anhydrous magnesium sulphate. Evaporation of the solvent under reduced pressure yielded ethyl 2,6-difluorobenzimidate as a pale yellow oil (6.0 g) which was used without further purification.

Workup

  1. customThe methylene chloride phase was separated
  2. dry with materialdried over anhydrous magnesium sulphate
  3. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8a539695aa0e4609a0e8e641fd967006
Source dataset
uspto-grants-1985_12
Patent number
US04559353

Reaction notes

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