Ethanol → 2-(Nitromethylene)-1-(phenylmethyl)imidazolidine

HRID 1259359Notes

Reaction equation

HRID 1259359 reaction equation
C(O)C.CS[C:6](SC)=[CH:7][N+:8]([O-:10])=[O:9].[CH2:13]([NH:20][CH2:21][CH2:22][NH2:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CO>C(Cl)(Cl)Cl>[CH2:13]([N:20]1[CH2:21][CH2:22][NH:23][C:6]1=[CH:7][N+:8]([O-:10])=[O:9])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 77801N-BenzylethylenediamineHCID 836231,1-Bis(methylthio)-2-nitroethylene

Product 1

HCID 534405852-(Nitromethylene)-1-(phenylmethyl)imidazolidineYield 74.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethanol (200 mL) was added to a solution of 1,1-bis-methylsulfanyl-2-nitro-ethene (14.5 g, 0.0878 mol) and N1-benzyl-ethane-1,2-diamine (12 g, 0.080 mol). The resulting mixture was heated to reflux for 2 hours. The reaction mixture was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was concentrated and the concentrate was dissolved in ethylacetate. The precipitate formed was collected and washed with ethylacetate to afford 13 g of the product (74.7% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe concentrate was dissolved in ethylacetate
  5. customThe precipitate formed
  6. customwas collected
  7. washwashed with ethylacetate

Sources & evidence

ORD record
ord-5b1e25965b324fa1b7a8c53a0227dd3c
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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