Triethylsilane → 4-Benzyl-5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-phenyl-pyrazole

HRID 350859Notes

Reaction equation

HRID 350859 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]=[C:12]([CH3:21])[C:11]=2[CH:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:22]([C:11]1[C:12]([CH3:21])=[N:13][N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]=1[S:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 10275058[5-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-phenyl-methanol

Product 1

HCID 102959674-Benzyl-5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-phenyl-pyrazoleYield 77.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution containing 80 mg of [5-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-phenyl-methanol and 64μof triethylsilane in 2 ml of trifluoroacetic acid was stirred at rt for 15 h. The mixture was concentrated, diluted with 10 ml of saturated sodium hydrogen carbonate solution and extracted twice with 10 ml of dichloromethane. Combined extracts were dried over magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using ethyl acetate/petroleum spirit 40°–60° C. (1:10) for the elution to give 60 mg of 4-benzyl-5-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-1H-pyrazole as a colourless gum. Mass spectrum (EI) m/z 424 [M]+.1H NMR (DMSO-d6) 2.26 (s, 3H), 3.88 (s, 2H), 6.77 (d, 2H), 7.13 (m, 3H), 7.20 (m, 2H), 7.32 (t, 1H), 7.35–7.48 (m, 5H).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with 10 ml of saturated sodium hydrogen carbonate solution
  3. extractionextracted twice with 10 ml of dichloromethane
  4. dry with materialCombined extracts were dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica gel
  8. customethyl acetate/petroleum spirit 40°–60° C. (1:10)
  9. washfor the elution

Sources & evidence

ORD record
ord-f51cd541712848798c215ff88f444b22
Source dataset
uspto-grants-2007_02
Patent number
US07183296B2

Reaction notes

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