Potassium Carbonate → [5-(3,5-dichloro-phenylsulfanyl)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-phenyl-methanone

HRID 47603

Reaction equation

Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].[Cl:22][C:23]1[CH:24]=[C:25]([SH:30])[CH:26]=[C:27]([Cl:29])[CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:22][C:23]1[CH:24]=[C:25]([S:30][C:2]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:5]=[C:4]([CH3:13])[C:3]=2[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])[CH:26]=[C:27]([Cl:29])[CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution containing 2.0 g of (5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-phenyl-methanone, 2.0 g of 3,5-dichlorothiophenol and 1.7 g of potassium carbonate in 50 ml of N,N-dimethylformamide was stirred at 60° C. for 19 h. The mixture was partitioned between 100 ml of water and 100 ml of dichloromethane. The organic layer was dried over magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using methanol/dichloromethane for the elution to give 2.2 g of [5-(3,5-dichloro-phenylsulfanyl)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-phenyl-methanone as a yellow oil. Mass spectrum (ES) m/z 439 [M+H]+, 480 [M+H+CH3CN]+.

Workup

customThe mixture was partitioned between 100 ml of water and 100 ml of dichloromethane
dry with materialThe organic layer was dried over magnesium sulphate
filtrationfiltered
customevaporated
customThe residue was purified by flash chromatography on silica gel
washfor the elution

Sources & evidence

ORD record: ord-6f91d18bce754f9c82ef74e264f8528d
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699887B2

Linked notes

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