2-Methylbenzamide → Benzenecarboximidic acid, 2-methyl-, ethyl ester

HRID 617640Notes

Reaction equation

HRID 617640 reaction equation
[C:1]1([CH3:10])[C:2]([C:7]([NH2:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.F[B-](F)(F)F.[CH2:16]([O+](CC)CC)[CH3:17]>ClCCl>[CH3:10][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[NH:9])[O:8][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 107042-MethylbenzamideHCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 12690380Benzenecarboximidic acid, 2-methyl-, ethyl esterYield 133%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of o-toluamide (13.5 g, 0.100 mol) in dichloromethane (150 mL) was added a solution (1.0 M, 106 mL, 0.106 mol) of triethyloxonium tetrafluoroborate in dichloromethane. The resulting mixture was stirred at room temperature for 14 h. Two-thirds of dichloromethane was evaporated under reduced pressure. After addition of ether (400 mL) to the concentrate, the mixture was stirred for 3 h under ice-cooling. Precipitates were collected by filtration, washed with ether, and dried in vacuo to give 21.7 g (86%) of ethyl 2-methylbenzimidate hydrotetrafluoroborate as a colorless solid.

Workup

  1. customTwo-thirds of dichloromethane was evaporated under reduced pressure
  2. additionAfter addition of ether (400 mL) to the concentrate
  3. stirringthe mixture was stirred for 3 h under ice-
  4. temperaturecooling
  5. customPrecipitates
  6. filtrationwere collected by filtration
  7. washwashed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-53d02a2dd54f4931b742aa5ac204913f
Source dataset
uspto-grants-1999_09
Patent number
US05948785

Reaction notes

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