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

HRID 1960270
Notes
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Reaction equation

HRID 1960270 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6342
Acetonitrile
Solvent

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-808957e757194187b7fe3fcdb355b9e5
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08410087B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes