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

HRID 504646Notes

Reaction equation

HRID 504646 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-fa1b1ed2389e43bb8c378cac1450d694
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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