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

HRID 1074202Notes

Reaction equation

HRID 1074202 reaction equation
[SH:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.Cl[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].C[O-].[Na+]>C(O)C>[N+:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[S:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 69451-Chloro-2-nitrobenzene2×HCID 10942334Sodium MethoxideHCID 178527877HCID 178527877, compound

Product 1

HCID 131782532-[(2-Nitrophenyl)sulfanyl]-1H-imidazoleYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.0 g (0.05 mole) of 2-mercaptoimidazole. 7.9 g (0.05 mole) of 2-chloronitrobenzene, 6.5 g (0.12 mole) of sodium methoxide and 150 ml of ethanol was stirred and refluxed for 5 hours. An additional 0.8 g of 2-chloronitrobenzene, was added and refluxing continued for 5 more hours. The mixture was filtered hot and the filtrates concentrated. The residue was partitioned with water and dichloromethane. The undissolved solid was collected by filtration to give 8.3 g of product. The dichloromethane was dried and concentrated. The residue was recrystallized from dichloromethane to give an additional 1.2 g of product. The total yield was 87% and the product was obtained as yellow rods, mp 178°-181° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperaturerefluxing
  3. filtrationThe mixture was filtered hot
  4. concentrationthe filtrates concentrated
  5. customThe residue was partitioned with water and dichloromethane
  6. filtrationThe undissolved solid was collected by filtration

Sources & evidence

ORD record
ord-bf4a1a1db1ca420fa00ba27b55179cc2
Source dataset
uspto-grants-1990_11
Patent number
US04973599

Reaction notes

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