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

HRID 1390722

反応式

HRID 1390722 の反応式
[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[C:10](=O)[N:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:6]1=[O:7].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:37]([O:45]C(=O)C1C=CC=NC=1)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[N:40][CH:39]=1.C(=O)(O)[O-].[Na+].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>CC(C)=O.ClCCl>[C:12]1([N:9]2[C:10]([C:39]3[C:38]([C:37]([OH:45])=[O:44])=[CH:43][CH:42]=[CH:41][N:40]=3)=[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])[C:6](=[O:7])[N:8]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

9

反応物 6

HCID 4781PhenylbutazoneHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 85607Nicotinic anhydrideHCID 516892Sodium Bicarbonate

生成物 1

HCID 203917051,2-Diphenyl-4-butyl-5-(3'-carboxypyridyl)-4-pyrazolin-3-one収率 77.5%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6344Dichloromethane溶媒

実験手順

Phenylbutazone (1,2-diphenyl-3,5-pyrazolidinedione; 11.00 g, 0.035 mole) was treated with 11.55 g (0.055 mole) of trifluoroacetic anhydride. The resulting solid suspension was shaken or mechanically stirred until a homogeneous solution was obtained, then it was stirred with a magnetic stirrer at room temperature in a tightly closed flask for one hour. The solution was concentrated in vacuo for one hour and the oily residue obtained was dissolved in 50 ml of acetone and allowed to react with 12.5 g (0.055 mole) of nicotinic anhydride. The initial suspension became homogeneous after 0.25 hours with concomitant formation of a yellow color. After an additional one hour at room temperature, the yellow solution was concentrated in vacuo and the residue was dissolved in 200 ml of dichloromethane. The dichloromethane solution was extracted first with an aqueous sodium bicarbonate solution (12.2 g, 0.145 mole in 150 ml), then with an aqueous sodium hydroxide solution (28 g, 0.07 mole in 56 ml) and subsequently dried over sodium sulfate. The dichloromethane solution was concentrated in vacuo and the residue was crystallized from dichloromethane petroleum ether bp 30-60° C to give 11.16 g (mp 139-141° C, 77.5% yield) of the title compound.

後処理

  1. stirringmechanically stirred until a homogeneous solution
  2. customwas obtained
  3. stirringit was stirred with a magnetic stirrer at room temperature in a tightly closed flask for one hour
  4. concentrationThe solution was concentrated in vacuo for one hour
  5. customthe oily residue obtained
  6. concentrationthe yellow solution was concentrated in vacuo
  7. dissolutionthe residue was dissolved in 200 ml of dichloromethane
  8. concentrationThe dichloromethane solution was concentrated in vacuo
  9. customthe residue was crystallized from dichloromethane petroleum ether bp 30-60° C

出典と根拠

ORDレコード
ord-cddef46dd4cb496296d05dbdfe819b8f
出典データセット
uspto-grants-1979_02
特許番号
US04139709

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