Ethylenediamine → 4-(benzylthio)-4-(nitromethyl)tetrahydro-2H-pyran

HRID 2238876Notes

Reaction equation

HRID 2238876 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[CH2:8]([SH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N+:16]([CH3:19])([O-:18])=[O:17].C(N)CN>C(#N)C>[CH2:8]([S:15][C:4]1([CH2:19][N+:16]([O-:18])=[O:17])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 6375NitromethaneHCID 7509Benzyl mercaptanHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 190249354-(benzylthio)-4-(nitromethyl)tetrahydro-2H-pyranYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tetrahydro-4H-pyran-4-one (10.3 g), benzylmercaptan (25.6 g), nitromethane (62.8 g), ethylenediamine (6.18 g) and acetonitrile (150 ml) was heated overnight under reflux. The reaction mixture was concentrated, and the obtained residue was subjected to silica gel column chromatography to give the title compound (17.6 g, yield 67%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (3:1, volume ratio).

Workup

  1. temperaturewas heated overnight
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d0a6d154d7514e6087defb42daac1710
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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