Diethyl Ether → Methyl 2-(4-chlorophenyl)-3-methylbutanimidate

HRID 894956Notes

Reaction equation

HRID 894956 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.F[B-](F)(F)F.[CH3:20][O+](C)C.CCOCC.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9](=[NH:11])[O:10][CH3:20])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 128981762-(4-Chlorophenyl)-3-methylbutanamide

Product 1

HCID 20571405Methyl 2-(4-chlorophenyl)-3-methylbutanimidate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

to a mixture of 2.32 g (11 mmol) of 2-(4-chlorophenyl)-3-methylbutyramide in methylene chloride is added, at room temperature, 1.78 g (12 mmol) of trimethyloxonium tetrafluoroborate. After stirring overnight under nitrogen, the resulting solution is poured onto an ice-cold mixture of ether, and aqueous sodium bicarbonate. The aqueous layer is discarded, and the ethereal layer is washed with cold water and dried over sodium sulfate. Filtration and concentration in vacuo affords methyl 2-(4-chlorophenyl)-3-methylbutanimidate.

Workup

  1. additionis added, at room temperature
  2. washthe ethereal layer is washed with cold water
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-fd54cb3f74bf4f57b94173f2e6d89c2e
Source dataset
uspto-grants-1981_08
Patent number
US04285879

Reaction notes

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