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

HRID 47630

반응식

HRID 47630 반응식
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

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27360963,5-DichlorobenzenethiolHCID 227475065-Chloro-1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde

생성물 1

HCID 227474955-(3,5-dichloro-phenylsulphanyl)-1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde수율 72.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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+CH3CN+H]+.

후처리

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

출처 및 근거

ORD 기록
ord-6b7b8d7a3416498d9f3bd90a8b03cd63
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699887B2

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