Phenylbutazone → 1,2-Diphenyl-4-butyl-5(4'-methylphenylsulfonyloxy)-4-pyrazolin-3-one

HRID 1076801

反応式

HRID 1076801 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.CN(C)C=O.[Tl+].[CH3:18][CH2:19][CH2:20][CH2:21][CH:22]1[C:27](=[O:28])[N:26]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:25]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:23]1=[O:24]>CCOCC>[C:35]1([N:25]2[C:23]([O:24][S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])=[C:22]([CH2:21][CH2:20][CH2:19][CH3:18])[C:27](=[O:28])[N:26]2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

参加物

6

反応物 4

HCID 4781Phenylbutazone2 回HCID 6228DimethylformamideHCID 73974-Toluenesulfonyl chlorideHCID 105005Thallous cation2 回

生成物 1

HCID 122520271,2-Diphenyl-4-butyl-5(4'-methylphenylsulfonyloxy)-4-pyrazolin-3-one収率 33%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Then, p-Toluenesulfonyl chloride (0.95 g, 5.0 mmole) was allowed to react with a dimethylformamide (20 ml) suspension of the Thallium (I) salt of phenylbutazone. Within a few minutes the solvent became pink and a yellow solid, instead of the white Thallium (I) salt of phenylbutazone, was observed suspended in the pink solution. The suspension was stirred overnight in a tightly sealed flask, then it was diluted with 100 ml of ether and filtered. The filtrate was concentrated in vacuo to remove the ether and the dimethylformamide was evaporated under a stream of nitrogen. The residue from the evaporation was suspended in dichloromethane and filtered. Analysis of the filtrate by TLC showed that it contained only one major component. The dichloromethane was evaporated in vacuo and the residue was crystallized from ether to give 0.76 g (mp 112°-121° C, 33% yield) of yellow crystals which contained only one component by TLC analysis. Recrystallization of the yellow crystals gave analytically pure crystals, mp 125°-127° C with spectral properties identical to the crystals, mp 112°-121° C.

後処理

  1. waitWithin a few minutes the solvent became pink
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto remove the ether
  5. customthe dimethylformamide was evaporated under a stream of nitrogen
  6. customThe residue from the evaporation
  7. filtrationfiltered
  8. customThe dichloromethane was evaporated in vacuo
  9. customthe residue was crystallized from ether

出典と根拠

ORDレコード
ord-dd8cee8602e64a1e85f0eb9dc3cf5b3b
出典データセット
uspto-grants-1976_05
特許番号
US03957803

関連ノート

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