1-Chloro-4-nitrobenzene → 2-[(4-Nitrophenyl)thio]-1H-imidazole

HRID 1158285Notes

Reaction equation

HRID 1158285 reaction equation
[SH:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([S:1][C:2]2[NH:3][CH:4]=[CH:5][N:6]=2)=[CH:9][CH:10]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 178527877HCID 178527877, compound

Product 1

HCID 150774982-[(4-Nitrophenyl)thio]-1H-imidazoleYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetonitrile (100 ml) suspension of 2-mercaptoimidazole (5.0 g) and 4-chloronitrobenzene (8.7 g), potassium carbonate (8.3 g) was stirred under refluxing for 1 day. The reaction mixture was poured into ice-water. The deposited solid matters were collected by filtration, washed with water and diethyl ether. The thus obtained solids were dried, there was obtained 2-(4-nitrophenylthio)imidazole (9.5 g, yield: 86%) as yellow powdery product.

Workup

  1. temperatureunder refluxing for 1 day
  2. filtrationThe deposited solid matters were collected by filtration
  3. washwashed with water and diethyl ether
  4. customThe thus obtained solids were dried

Sources & evidence

ORD record
ord-3cc6f21b15074536bcb4517bc8d2c4af
Source dataset
uspto-grants-2010_10
Patent number
US07807843B2

Reaction notes

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