2-[(4-Nitrophenyl)thio]-1H-imidazole → HCID 23080269, compound

HRID 1158288Notes

Reaction equation

HRID 1158288 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]>C(#N)C=C>[C:4]([CH2:5][CH2:6][N:15]1[CH:14]=[CH:13][N:12]=[C:11]1[S:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)#[N:1]

Participants

3

Reactant 1

HCID 150774982-[(4-Nitrophenyl)thio]-1H-imidazole

Product 1

HCID 23080269HCID 23080269, compoundYield 146.5%

Reagents, catalysts & solvents 1

HCID 7855AcrylonitrileSolvent

Procedure

To acrylonitrile (10 ml) suspension of 2-(4-nitrophenylthio)imidazole (500 mg) was added 1,8-diazabicyclo[5.4.0]undecene-7 (0.04 ml), the reaction mixture was stirred for 1 hour under refluxing. The residue obtained by concentration was purified by use of a basic silica gel column chromatography (eluent: dichloromethane), the thus obtained solid was recrystallized from dichloromethane-tert-butylmethyl ether, there was obtained 1-(2-cyanoethyl)-2-(4-nitrophenylthio)imidazole (454 mg, yield: 74%) as colorless granular product.

Workup

  1. temperatureunder refluxing
  2. customThe residue obtained by concentration
  3. customwas purified by use of a basic silica gel column chromatography (eluent: dichloromethane)
  4. customthe thus obtained solid was recrystallized from dichloromethane-tert-butylmethyl ether

Sources & evidence

ORD record
ord-5b7e2d1a28414b67868d782ff869a916
Source dataset
uspto-grants-2010_10
Patent number
US07807843B2

Reaction notes

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