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

HRID 350870

反応式

HRID 350870 の反応式
Cl[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([CH3:16])[C:3]=1[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18].C(=O)([O-])[O-].[K+].[K+].[Cl:31][C:32]1[CH:33]=[C:34]([SH:39])[CH:35]=[C:36]([Cl:38])[CH:37]=1>CN(C)C=O>[Cl:31][C:32]1[CH:33]=[C:34]([S:39][C:2]2[N:6]([CH2:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)[N:5]=[C:4]([CH3:16])[C:3]=2[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH:35]=[C:36]([Cl:38])[CH:37]=1

参加物

5

反応物 3

HCID 11430Potassium Carbonate3 回HCID 27360963,5-Dichlorobenzenethiol3 回HCID 22747458[5-chloro-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

生成物 1

HCID 22747490[5-(3,5-dichlorophenylthio)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone収率 58.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A solution containing 170 mg of [5-chloro-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone in 10 ml of N,N-dimethylformamide was treated with 83 mg of potassium carbonate and 107 mg of 3,5-dichlorothiophenol. The mixture was heated at 100° C. for 4 h. The mixture was treated with a further 83 mg of potassium carbonate and 107 mg of 3,5-dichlorothiophenol. The mixture was then heated at 50° C. for 64 h. The mixture was treated with a further 83 mg of potassium carbonate and 107 mg of 3,5-dichlorothiophenol. The mixture was then heated at 100° C. for 2 h. The solvent was removed under reduced pressure and residue partitioned between dichloromethane/water, washed with brine then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified via flash chromatography on silica gel using diethyl ether/petroleum ether (1:4 to 1:3) to give 140 mg of [5-(3,5-dichlorophenylthio)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone as a colourless oil. Mass spectrum (ES) m/z 483[M+H]+.

後処理

  1. temperatureThe mixture was then heated at 50° C. for 64 h
  2. temperatureThe mixture was then heated at 100° C. for 2 h
  3. customThe solvent was removed under reduced pressure and residue
  4. custompartitioned between dichloromethane/water
  5. washwashed with brine
  6. dry with materialthen dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified via flash chromatography on silica gel

出典と根拠

ORDレコード
ord-daeff3c98afd48029da2ce9a9f309d8b
出典データセット
uspto-grants-2007_02
特許番号
US07183296B2

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