4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → HCID 12832302, compound

HRID 370764Notes

Reaction equation

HRID 370764 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].[CH3:15][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]([CH3:33])=[CH:29][CH:28]=2)=[CH:18][CH:17]=1.[H-].[Na+]>CN(C)C=O>[CH3:33][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]([CH3:15])=[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 178424005HCID 178424005, compound

Product 1

HCID 12832302HCID 12832302, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under agitation and covering with argon, a solution of 4.52 g of 4-chloro-3-nitrotrifluoromethylbenzene in 25 ml of dimethylformamide is added dropwise to a solution of 5.61 g of 4,5-bis(4-methylphenyl)-2-mercaptoimidazole and 0.6 g of sodium hydride (80% strength in white oil) in 200 ml of dimethylformamide. The solution is further stirred for 30 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 ethanol, thus producing 8.26 g of 4,5-bis(4-methylphenyl)-2-(2-nitro-4-trifluoromethylphenylthio)imidazole in fine yellow needles having a decomposition point of 252°.

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 ethanol

Sources & evidence

ORD record
ord-e9a614b665f1490db94e20687c69fb4e
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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