Water → [(4-Nitrophenyl)sulfanyl]acetonitrile

HRID 856687Notes

Reaction equation

HRID 856687 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:11]([N:13](CC)CC)[CH3:12].BrCC#N.O>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:12][C:11]#[N:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11534BromoacetonitrileHCID 158094-Nitrobenzenethiol

Product 1

HCID 13068864[(4-Nitrophenyl)sulfanyl]acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-nitrobenzenethiol (10 g) was dissolved in THF (100 ml), and to this solution was added triethylamine (12.6 ml) and then, bromoacetonitrile (5.4 ml), and the mixture was stirred for 30 minutes. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was washed with hexane/ethyl acetate, to give 2-[(4-nitrophenyl)sulfanyl]acetonitrile (10.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. washthe obtained residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-f1d40b76166c433394c10331f5cf239c
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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