Ethylenediamine → ({[2,2-Dimethoxy-1-methyl-1-(nitromethyl)ethyl]thio}methyl)benzene

HRID 1960259Notes

Reaction equation

HRID 1960259 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[C:4]([CH3:6])=O.[CH2:9]([SH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N+:17]([CH3:20])([O-:19])=[O:18].C(N)CN>C(#N)C>[CH3:1][O:2][CH:3]([O:7][CH3:8])[C:4]([S:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:6])[CH2:20][N+:17]([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 6375NitromethaneHCID 7509Benzyl mercaptanHCID 80650Pyruvic aldehyde dimethyl acetal

Product 1

HCID 59135973({[2,2-Dimethoxy-1-methyl-1-(nitromethyl)ethyl]thio}methyl)benzeneYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1,1-dimethoxyacetone (5.00 ml), benzylmercaptan (5.50 ml), nitromethane (23 ml), ethylenediamine (3.00 ml) and acetonitrile (15 ml) was stirred at room temperature, and then overnight at 80° C. The reaction mixture was concentrated, and the obtained residue was subjected to silica gel column chromatography to give the title compound (5.81 g, yield 48%) as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:6, volume ratio).

Workup

  1. customovernight
  2. customat 80° C
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-65388a29f0a2436782cd2d64ab43b80a
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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