Ethanol → HCID 86617335, compound

HRID 1960214Notes

Reaction equation

HRID 1960214 reaction equation
[Na].[C:2]1([SH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[CH2:12]([O:19][N:20]=[C:21](Br)[CH:22]=[CH:23][S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[CH2:12]([O:19][N:20]=[C:21]([S:8][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:22]=[CH:23][S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 7969ThiophenolHCID 5360545SodiumHCID 86617336N-benzyloxy-3-(phenylthio)acrylimidoyl bromide

Product 1

HCID 86617335HCID 86617335, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Sodium salt of thiophenol (0.14 g) was added to ethanol (5 ml) solution of N-benzyloxy-3-phenylthioacrylimidoyl bromide (0.30 g) at room temperature, then it was heat refluxing for three hours. It was cooled, and chloroform (50 ml) was added to the reaction mixture. It was successively washed with 1N aqueous sodium hydroxide solution, pure water, aqueous saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain phenyl N-benzyloxy-3-(phenylthio)thioacrylimidate (0.14 g) as colorless oil.

Workup

  1. temperatureit was heat
  2. temperaturerefluxing for three hours
  3. temperatureIt was cooled
  4. washIt was successively washed with 1N aqueous sodium hydroxide solution, pure water, aqueous saturated sodium chloride solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-14aeb4de498f493fa025b82da578e928
Source dataset
uspto-grants-2013_04
Patent number
US08410316B2

Reaction notes

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