Methanethiol → phenyl 3-methylthio-N-phenylacrylimidate

HRID 1960205Notes

Reaction equation

HRID 1960205 reaction equation
O([CH:8]=[CH:9][C:10](=[N:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C1C=CC=CC=1.C1COCC1.[Na].[CH3:31][SH:32]>C(OCC)(=O)C>[CH3:31][S:32][CH:8]=[CH:9][C:10](=[N:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 878MethanethiolHCID 8028TetrahydrofuranHCID 5360545SodiumHCID 69127142Phenyl 3-phenoxy-N-phenylacrylimidate

Product 1

HCID 69126846phenyl 3-methylthio-N-phenylacrylimidateYield 78.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phenyl 3-phenoxy-N-phenylacrylimidate (0.30 g) was dissolved to THF (5 ml), sodium salt of methyl mercaptan (0.075 g) was added thereto and stirred for four hours at room temperature. Ethyl acetate (50 ml) was added to the reaction solution, and it was successively washed with water and aqueous saturated of 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-methylthio-N-phenylacrylimidate (0.20 g) as yellow oil.

Workup

  1. additionwas added
  2. washwas successively washed with water and aqueous saturated of sodium chloride solution
  3. dry with materialdried over magnesium sulfate (anhydrous)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a17dfb6c9b944daabed64fba693042c5
Source dataset
uspto-grants-2013_04
Patent number
US08410316B2

Reaction notes

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