4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → HCID 12832298, compound

HRID 1995191Notes

Reaction equation

HRID 1995191 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].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]=[C:24]([SH:34])[NH:25][C:26]=2[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[CH:18][CH:17]=1.[H-].[Na+]>CN(C)C=O>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:26]2[N:25]=[C:24]([S:34][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:23][C:22]=2[C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 24758Sodium hydrideHCID 178527835HCID 178527835, compound

Product 1

HCID 12832298HCID 12832298, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under agitation and a layer of argon, a solution of 3.77 g of 4-chloro-3-nitrotrifluoromethylbenzene in 50 ml of dimethylformamide is added dropwise to a solution of 4.82 g of 4,5-bis(4-chlorophenyl)-2-mercaptoimidazole and 0.45 g of sodium hydride (80% strength in white oil) in 100 ml of dimethylformamide. The mixture is stirred for 20 minutes, concentrated under vacuum, and the residue is 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 methylene chloride/ether, thus obtaining 6.82 g of 4,5-bis(4-chlorophenyl)-2-(2-nitro-4-trifluoromethylphenylthio)imidazole, mp 264°-266°.

Workup

  1. concentrationconcentrated under vacuum
  2. dry with materialThe organic solution is dried over sodium sulfate
  3. concentrationconcentrated to dryness under vacuum
  4. customThe residue is crystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-fc64108027334e2e80d50f84579e1a08
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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