2-Methylbenzamide → Ethyl 2-methyl-benzimidate tetrafluoroborate

HRID 1167347Notes

Reaction equation

HRID 1167347 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:11][B-:12]([F:15])([F:14])[F:13].[CH2:16]([O+](CC)CC)[CH3:17]>C(Cl)Cl>[F:11][B-:12]([F:15])([F:14])[F:13].[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 22996236Ethyl 2-methyl-benzimidate tetrafluoroborateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a degassed suspension of o-toluamide (1.35 g, 9.788 mmol) in methylene chloride (5 mL) was added triethyloxonium tetrafluoroborate (9.788 mL, 9.788 mmol, 1 M in methylene chloride). After the clear solution was stirred at room temperature overnight, it was concentrated in vacuo. The residue was triturated in methylene chloride and diethyl ether. The white solid was filtered off and washed with diethyl ether to afford ethyl 2-methyl-benzimidate tetrafluoroborate (1.4 g, 80%). It was used without further purification.

Workup

  1. concentrationit was concentrated in vacuo
  2. customThe residue was triturated in methylene chloride
  3. filtrationThe white solid was filtered off
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f07fac63b95c4d7095a5177695724233
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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