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

HRID 462555
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HRID 462555 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]([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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매
HCID 962
Water
용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5d2d7edd105b48e1a0e03c2ab17533c7
출처 데이터셋
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04515948

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