Dimethyl Sulfoxide → 3',5'-Dimethoxy-4'-(methylamino)-2-(methylsulfonyl)-acetophenone

HRID 542973ノート

反応式

HRID 542973 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]([O:21][CH3:22])[C:18]([NH:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1>C(O)(=O)C.O>[CH3:26][O:25][C:17]1[CH:16]=[C:15]([C:14](=[O:13])[CH2:1][S:2]([CH3:5])(=[O:4])=[O:3])[CH:20]=[C:19]([O:21][CH3:22])[C:18]=1[NH:23][CH3:24]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 53774973Methyl 3,5-dimethoxy-4-(methylamino)benzoate

生成物 1

HCID 212809593',5'-Dimethoxy-4'-(methylamino)-2-(methylsulfonyl)-acetophenone

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

A suspension of 44.2 g. of dimethylsulfone and 16 g. of sodium hydride (50% dispersion in oil) in 150 ml. of absolute dimethylsulfoxide was stirred at 50° C. for 4 hours under an atmosphere of nitrogen and the exclusion of moisture. 30.4 g. of 3,5-dimethoxy-4-(methylamino)-benzoic acid methyl ester were added and the mixture was stirred at 80° C. for 10 minutes and at 25° C. for 30 minutes. The mixture was then dissolved in 600 ml. of water and the solution was made neutral by the addition of glacial acetic acid. The precipitate was removed by filtration with suction, washed with water, dried and recrystallized from ethyl acetate, whereby there was obtained 3',5'-dimethoxy-4'-(methylamino)-2-(methylsulfonyl)-acetophenone having a melting point of 98°-99° C.

後処理

  1. additionA suspension of 44.2 g
  2. dissolutionThe mixture was then dissolved in 600 ml
  3. customThe precipitate was removed by filtration with suction
  4. washwashed with water
  5. customdried
  6. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-9a304e4dfa9142b889d3fe408a09a4e6
出典データセット
uspto-grants-1987_04
特許番号
US04659818

反応ノート

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