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Dimethyl Sulfoxide → 4'-Amino-3',5'-dimethyl-2-(methylsulfonyl)-acetophenone

HRID 462555
ノート
印刷プレビュー

反応式

HRID 462555 の反応式
[CH3:1][S:2]([CH3:5])(=[O:4])=[O:3].[H-].[Na+].CS(C)=O.C[O:13][C:14](=O)[C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([NH2:22])=[C:17]([CH3:23])[CH:16]=1>C(O)(=O)C.O>[NH2:22][C:18]1[C:19]([CH3:21])=[CH:20][C:15]([C:14](=[O:13])[CH2:1][S:2]([CH3:5])(=[O:4])=[O:3])=[CH:16][C:17]=1[CH3:23]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 11030398Benzoic acid, 4-amino-3,5-dimethyl-, methyl ester

生成物 1

HCID 212810124'-Amino-3',5'-dimethyl-2-(methylsulfonyl)-acetophenone

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒
HCID 962
Water
溶媒

反応条件

温度
80 °C

実験手順

A suspension of 33 g. of dimethylsulfone and 11 g. of sodium hydride (50% dispersion in oil) in 160 ml. of absolute dimethylsulfoxide was stirred at 50° C. under an atmosphere of nitrogen and the exclusion of moisture for 3 hours. Then, 18 g. of 4-amino-3,5-dimethyl-benzoic acid methyl ester were added. The mixture was stirred at 80° C. for 30 minutes and at room temperature for 1 hour and then dissolved in 400 ml. of water. The solution was neutralized with glacial acetic acid. The precipitate which formed was removed by filtration with suction, washed with water, dried and recrystallized from ethyl acetate, whereby there was obtained 4'-amino-3',5'-dimethyl-2-(methylsulfonyl)-acetophenone having a melting point of 179°-180° C.

後処理

  1. additionA suspension of 33 g
  2. dissolutiondissolved in 400 ml
  3. customThe precipitate which formed
  4. customwas removed by filtration with suction
  5. washwashed with water
  6. customdried
  7. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-5d2d7edd105b48e1a0e03c2ab17533c7
出典データセット
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04515948

反応ノート

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