Nitromethane → HCID 13956609, compound

HRID 2061649Notes

Reaction equation

HRID 2061649 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:8]([CH3:11])([O-:10])=[O:9].N1CCCCC1.[CH2:18]([SH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[N+:8]([CH2:11][CH:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[S:25][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 7509Benzyl mercaptanHCID 7967CyclohexanoneHCID 8082Piperidine

Product 1

HCID 13956609HCID 13956609, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.05 ml (10 mmol) of cyclohexanone, 5.5 ml (101 mmol) of nitromethane, 2.1 ml (21 mmol) of piperidine are added to a solution of 5 ml (42 mmol) of benzylmercaptan in 20 ml of acetonitrile. The solution is refluxed for 4 h. At room temperature, the mixture is evaporated and the residue is chromatographed on silica gel (heptane then heptane/ethyl acetate, 50/50, v/v). 600 mg of (1-nitromethyl-cyclohexylsulfanylmethyl)-benzene is obtained in the form of a colorless oil. (Yield=22%).

Workup

  1. temperatureThe solution is refluxed for 4 h
  2. customAt room temperature, the mixture is evaporated
  3. customthe residue is chromatographed on silica gel (heptane

Sources & evidence

ORD record
ord-0bbe2f65a0e243c6a7b64f81e59af348
Source dataset
uspto-grants-2012_10
Patent number
US08283378B2

Reaction notes

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