4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → HCID 12832303, compound

HRID 370765Notes

Reaction equation

HRID 370765 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][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[C:25]([SH:36])[NH:26][C:27]=2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[CH:19][CH:18]=1.[H-].[Na+]>CN(C)C=O>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([C:27]2[N:26]=[C:25]([S:36][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:23]=2[C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 24758Sodium hydrideHCID 178489021HCID 178489021, compound

Product 1

HCID 12832303HCID 12832303, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under agitation and a layer of argon, a solution of 4.52 g of 4-chloro-3-nitrotrifluoromethylbenzene in 25 ml of dimethylformamide is added dropwise to a solution of 6.25 g of 4,5-bis(4-methoxyphenyl)-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 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 hexane/acetone, thus obtaining 9.44 g of 4,5-bis(4-methoxyphenyl)-2-(2-nitro-4-trifluoromethylphenylthio)imidazole in yellow needles, 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 hexane/acetone

Sources & evidence

ORD record
ord-605614bf45cf4399a1bd5cae3fd41e78
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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