Ethylenediamine → HCID 59136148, compound

HRID 1960338Notes

Reaction equation

HRID 1960338 reaction equation
[O:1]1[C:5]2([CH2:10][C:9](=O)[CH2:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH2:12]([SH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N+:20]([CH3:23])([O-:22])=[O:21].C(N)CN>C(#N)C>[CH2:12]([S:19][C:8]1([CH2:23][N+:20]([O-:22])=[O:21])[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 6375NitromethaneHCID 7509Benzyl mercaptanHCID 2406021,4-Dioxaspiro[4.5]decan-7-one

Product 1

HCID 59136148HCID 59136148, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1,4-dioxaspiro[4.5]decan-9-one (6.00 g), benzylmercaptan (5.00 mL), nitromethane (20 mL), ethylenediamine (2.83 mL) and acetonitrile (25 mL) was heated under reflux for 3 hr. The reaction mixture was concentrated, and the obtained residue was subjected to silica gel column chromatography to give the title compound (8.96 g, yield 72%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio). melting point 121-122° C.

Workup

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

Sources & evidence

ORD record
ord-da9286521b2d47ff928558a60491ec05
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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