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

HRID 542973노트

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HRID 542973 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9a304e4dfa9142b889d3fe408a09a4e6
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04659818

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