Ethylenediamine → HCID 57475979, compound

HRID 1960258Notes

Reaction equation

HRID 1960258 reaction equation
[CH3:1][C:2](=O)[CH:3]=[CH2:4].[NH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[CH2:12]([SH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N)CN.[N+:24]([CH3:27])([O-:26])=[O:25]>C(#N)C>[CH2:12]([S:19][C:2]([CH3:1])([CH2:27][N+:24]([O-:26])=[O:25])[CH2:3][CH2:4][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 3301EthylenediamineHCID 6375NitromethaneHCID 6570Methyl vinyl ketoneHCID 7509Benzyl mercaptanHCID 8083Morpholine

Product 1

HCID 57475979HCID 57475979, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-buten-2-one (2.00 ml) and morpholine (2.35 ml) was stirred at room temperature for 30 min (exothermic reaction). Benzylmercaptan (3.20 ml), nitromethane (13.2 ml), ethylenediamine (1.8 ml) and acetonitrile (10 ml) were added to the reaction mixture, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, and the obtained residue was subjected to silica gel column chromatography to give the title compound (3.27 g, yield 41%) as a yellow oil from a fraction eluted with ethyl acetate.

Workup

  1. custom(exothermic reaction)
  2. stirringthe mixture was stirred overnight at room temperature
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-dcefa61e1a6d463bae8619d6149d03cf
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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