Dimethylformamide → HCID 69128292, compound

HRID 1918444Notes

Reaction equation

HRID 1918444 reaction equation
C(S)C.[CH2:4]([S:6][CH:7]=[CH:8][C:9](=[N:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:5].CN(C=O)C.[H-].[Na+].O(C=CC(=NC1C=CC=CC=1)OC1C=CC=CC=1)C1C=CC=CC=1>C(OCC)(=O)C>[CH2:4]([S:6][CH:7]=[CH:8][C:9](=[N:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[O:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:5]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 69127142Phenyl 3-phenoxy-N-phenylacrylimidateHCID 86686876HCID 86686876, compound

Product 1

HCID 69128292HCID 69128292, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phenyl 3-ethylthio-N-phenylacrylimidate Ethanethiol (0.11 ml) was dissolved to DMF (3 ml), and sodium hydride (60% in oil: 60 mg) was added under ice-cooling, and stirred for 30 minutes at the same temperature. Phenyl 3-phenoxy-N-phenylacrylimidate (0.30 g) was dissolved to DMF (2 ml), and the obtained solution was added to the above mentioned thiolate solution under ice-cooling, and stirred for two hours at the same temperature and for two hours at room temperature. Ethyl acetate (100 ml) was added to the reaction solution, and it was successively washed with 1N aqueous sodium hydroxide solution, water and aqueous saturated sodium chloride solution, dried over magnesium sulfate (anhydrous), concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain phenyl 3-ethylthio-N-phenylacrylimidate (0.14 g) as yellow oil.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. additionthe obtained solution was added to the
  4. temperaturecooling
  5. stirringstirred for two hours at the same temperature and for two hours at room temperature
  6. washwas successively washed with 1N aqueous sodium hydroxide solution, water and aqueous saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate (anhydrous)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79e293d3c7cd47e18780e741d9dad3c9
Source dataset
uspto-grants-2013_12
Patent number
US08618329B2

Reaction notes

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