Water → 5-(3,5-dichloro-phenylsulphanyl)-1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde

HRID 350887Notes

Reaction equation

Cl[C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[C:4]([CH3:9])[C:3]=1[CH:10]=[O:11].[Cl:12][C:13]1[CH:14]=[C:15]([SH:20])[CH:16]=[C:17]([Cl:19])[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:12][C:13]1[CH:14]=[C:15]([S:20][C:2]2[N:6]([CH2:7][CH3:8])[N:5]=[C:4]([CH3:9])[C:3]=2[CH:10]=[O:11])[CH:16]=[C:17]([Cl:19])[CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 9.2 g of 5-chloro-1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde, 14.3 g of 3,5-dichlorothiophenol and 11.8 g of potassium carbonate in 40 ml of anhydrous N,N-dimethylformamide was stirred under nitrogen at 100° C. for 18 hours. Water (200 ml) was added and the mixture was extracted three times with 100 ml of dichloromethane. The combined extracts were dried over magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using dichloromethane/petroleum ether (bp 40–60° C.) for the elution to give 12.2 g of 5-(3,5-dichloro-phenylsulphanyl)-1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde as an orange solid. Mass spectrum (ES) m/z 356 [M+CH3CH+H]+.

Workup

extractionthe mixture was extracted three times with 100 ml of dichloromethane
dry with materialThe combined extracts were dried over magnesium sulphate
filtrationfiltered
customevaporated
customThe residue was purified by flash chromatography on silica gel
washfor the elution

Sources & evidence

ORD record: ord-95b2ae22c5c745bcbcd022c45c8414b3
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183296B2

Reaction notes

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