N-Benzylformamide → Ethyl N-Benzylformimidate

HRID 1701588Notes

Reaction equation

HRID 1701588 reaction equation
[CH2:1]([NH:8][CH:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.[CH2:16]([O+](CC)CC)[CH3:17]>C(Cl)Cl>[CH2:1]([N:8]=[CH:9][O:10][CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 80654N-BenzylformamideHCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 19022221Ethyl N-Benzylformimidate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 690 mg (5.1 mmoles) of N-benzylformamide in 5 ml of methylene chloride is cooled in an ice-water bath and put under an argon blanket. The solution is stirred while 4.9 ml (4.9 mmoles) of 1 M triethyloxonium fluoroborate in methylene chloride is added dropwise. After a 45 minute reaction time, the mixture is concentrated to dryness under reduced pressure at room temperature, and the residue is dried under reduced pressure over P2O5. The nuclear magnetic resonance spectrum of the product in deuterochloroform is fully in accord with the product being a fluoroborate etherate complex of ethyl N-benzylformimidate.

Workup

  1. additionis added dropwise
  2. customAfter a 45 minute reaction time
  3. concentrationthe mixture is concentrated to dryness under reduced pressure at room temperature
  4. dry with materialthe residue is dried under reduced pressure over P2O5

Sources & evidence

ORD record
ord-db3c0f88c7884ec3acc461c5d9551a24
Source dataset
uspto-grants-1980_03
Patent number
US04194047

Reaction notes

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