p-Fluoronitrobenzene → 2-[(4-Nitrophenyl)thio]-1H-imidazole

HRID 1074198Notes

Reaction equation

HRID 1074198 reaction equation
C[O-].[Na+].[SH:4][C:5]1[NH:6][CH:7]=[CH:8][N:9]=1.F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1>C(O)C>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([S:4][C:5]2[NH:6][CH:7]=[CH:8][N:9]=2)=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 10942334Sodium MethoxideHCID 178527877HCID 178527877, compound

Product 1

HCID 150774982-[(4-Nitrophenyl)thio]-1H-imidazoleYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 6.2 g (0.12 mmoles) of sodium methoxide and 90 ml of ethyl alcohol was added 5.8 g (0 058 mmoles) of 2-mercaptoimidazole. After stirring for 0.5 hour, 8.2 g (0.058 mole) of 1-fluoro-4-nitrobenzene was added and the mixture refluxed for 4 hours. The mixture was allowed to cool and filtered to give 5.0 g (39%) of the product. An additional 2.0 g (16%) of product was recovered from the filtrates. Recrystallization from dichloromethane/methanol gave the product as yellow rods. mp 207°-209° C.

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. temperatureto cool
  3. filtrationfiltered

Sources & evidence

ORD record
ord-fe827475469e4014ba7c1b1634f527ec
Source dataset
uspto-grants-1990_11
Patent number
US04973599

Reaction notes

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