Ethylenediamine → 3-(Benzylthio)-3-methyl-4-nitrobutan-1-ol

HRID 1994686

Reaction equation

HRID 1994686 reaction equation
[OH:1][CH2:2][CH2:3][C:4](=O)[CH3:5].[CH2:7]([SH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N+:15]([CH3:18])([O-:17])=[O:16].C(N)CN>C(#N)C>[CH2:7]([S:14][C:4]([CH3:5])([CH2:18][N+:15]([O-:17])=[O:16])[CH2:3][CH2:2][OH:1])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 6375NitromethaneHCID 7509Benzyl mercaptanHCID 1115094-Hydroxy-2-Butanone

Product 1

HCID 574759763-(Benzylthio)-3-methyl-4-nitrobutan-1-olYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-hydroxy-2-butanone (5.00 g), benzylmercaptan (6.65 ml), nitromethane (30.7 ml), ethylenediamine (3.80 ml) and acetonitrile (30 ml) was stirred at room temperature for 4 hr. The reaction mixture was concentrated, and the obtained residue was subjected to silica gel column chromatography to give the title compound (5.70 g, yield 39%) as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-6d730107947a48af9f4db43f279af840
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Linked notes

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