Potassium Carbonate → HCID 53920625, compound

HRID 581108Notes

Reaction equation

HRID 581108 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[S:13])[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[CH:26][O:27][CH3:28])[C:23]([O-:25])=[O:24].[C:29](=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:8][N:9]=[C:10]([S:13][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[CH:26][O:27][CH3:28])[C:23]([O:25][CH3:29])=[O:24])[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 19606573HCID 19606573, compoundHCID 73517220HCID 73517220, compound

Product 1

HCID 53920625HCID 53920625, compoundYield 67%

Procedure

A mixture of N-benzyloxythiopropionamide (1.2 g, 6 mmol) prepared as above, 2-bromomethylphenyl-3-methoxypropenoate (1.7 g, 6 mmol) and potassium carbonate (1 g, 7 mmol) was stirred overnight at room temperature. The reaction mixture was filtered, the solvent was removed by evaporation, and the residue was purified with silica gel chromatography to obtain methyl 2-[2-{(1-benzyloxyiminopropyl)thiomethyl}phenyl]-3-methoxypropenoate (1.6 g, yield: 67%). The proton NMR Spectra: 1.12 t (3H); 2.36 q (2H); 3.67 s (3H); 3.77 s (3H); 3.95 s (2H); 5.12 s (2H); 7.15-7.50 m (9H); 7.59 s (1H) (Solvent: CDCl3).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed by evaporation
  3. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-b0c9f3e25bc848bb8030f2ae859c1d41
Source dataset
uspto-grants-1999_07
Patent number
US05919825

Reaction notes

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