4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → 4,5-Diphenyl-2-(2-nitro-4-trifluoromethylphenylthio)imidazole

HRID 1995192Notes

Reaction equation

HRID 1995192 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]1([C:21]2[N:22]=[C:23]([SH:32])[NH:24][C:25]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+]>CN(C)C=O>[C:15]1([C:21]2[N:22]=[C:23]([S:32][C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=3[N+:12]([O-:14])=[O:13])[NH:24][C:25]=2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 24758Sodium hydrideHCID 178527825HCID 178527825, compound

Product 1

HCID 128322994,5-Diphenyl-2-(2-nitro-4-trifluoromethylphenylthio)imidazoleYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under stirring and a layer of argon, a solution of 7.45 g of 4-chloro-3-nitrotrifluoromethylbenzene in 40 ml of dimethylformamide is added dropwise to a solution of 7.94 g of 4,5-diphenyl-2-mercaptoimidazole and 0.45 g of sodium hydride (80% strength in white oil) in 150 ml of dimethylformamide. The mixture is agitated for 20 minutes, concentrated under vacuum, and the residue distributed between water and ethyl acetate. The organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is crystallized from ether, thus obtaining 11.87 g of 4,5-diphenyl-2-(2-nitro-4-trifluoromethylphenylthio)imidazole, mp 234°-236°.

Workup

  1. stirringThe mixture is agitated for 20 minutes
  2. concentrationconcentrated under vacuum
  3. dry with materialThe organic solution is dried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-2e94bdb1f77640c3a658d796e1a51d62
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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