5-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-4-styryl-1H-pyrazole → 5-(3,5-Dichlorophenyl)sulfanyl-3-methyl-4-phenethyl-1-phenyl-pyrazole

HRID 47605Notes

Reaction equation

HRID 47605 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]=[CH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1>[Pd].C(OCC)(=O)C>[Cl:8][C:6]1[CH:5]=[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[CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 1

HCID 695160655-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-4-styryl-1H-pyrazole

Product 1

HCID 101140825-(3,5-Dichlorophenyl)sulfanyl-3-methyl-4-phenethyl-1-phenyl-pyrazoleYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension containing 95 mg of 5-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-4-styryl-1H-pyrazole and 75 mg of 10% palladium on activated carbon in 10 ml of ethyl acetate was stirred under hydrogen (1 atm) at rt for 40 h. The suspension was filtered on Celite® and the filtrate was evaporated to leave 89 mg of 5-(3,5-dichlorophenylthio)-3-methyl-4-(2-phenylethyl)-1-phenyl-1H-pyrazole as a colourless gum. Mass spectrum (EI) m/z 438[M]+. 1H NMR (DMSO-d6) 2.14 (s, 3H), 2.68 (t, 2H), 2.77 (t, 2H), 6.85 (d, 2H), 7.09 (d, 2H), 7.16 (t, 1H), 7.24 (t, 2H), 7.33-7.48 (m, 6H).

Workup

  1. filtrationThe suspension was filtered on Celite®
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-7f2680c3541040d894f5900758a0ada0
Source dataset
uspto-grants-2004_03
Patent number
US06699887B2

Reaction notes

Loading…