Dimethylformamide → 4-(4-Isopropyl-phenyl)-1-(3-methane-sulphonyl-benzyl)-5-propargyloxy-phenyl-methanone

HRID 641819노트

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HRID 641819 반응식
N[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]#[CH:11])=C[C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=O.[C:23]([O-:26])([O-])=O.[K+].[K+].Cl[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([S:36]([CH3:39])(=[O:38])=[O:37])[C:31]=1C.[CH3:41]N(C)C=O>>[CH:20]([C:17]1[CH:16]=[CH:15][C:14]([C:12]2[C:5]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:7]([CH:23]=[O:26])([CH2:41][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([S:36]([CH3:39])(=[O:37])=[O:38])[CH:31]=3)[CH2:2][CH:3]=2)=[CH:19][CH:18]=1)([CH3:21])[CH3:22]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 213497981-Chloro-methyl-3-methanesulphonyl-benzeneHCID 45139628(2-Amino-5-(prop-2-yn-1-yloxy)phenyl)(4-isopropylphenyl)methanone

생성물 1

HCID 866043814-(4-Isopropyl-phenyl)-1-(3-methane-sulphonyl-benzyl)-5-propargyloxy-phenyl-methanone

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온도
100 °C

실험 절차

A mixture of 100 mg (0.34 mmol) (2-amino-5-propargyloxy-phenyl)-(4-isopropyl-phenyl)-methanone, 80 mg (0.58 mmol) K2CO3 and 77 mg (0.375 mmol) 1-chloro-methyl-3-methanesulphonyl-benzene in 1 ml dimethylformamide is stirred at 80° C. for 6 h and at 100° C. for 3 h. Then the reaction mixture is poured onto water and extracted with ethyl acetate. The combined organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1) to afford the title compound as a yellow foam.

후처리

  1. additionThen the reaction mixture is poured onto water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1)

출처 및 근거

ORD 기록
ord-3fa8ad21a69a455aa883827b1a5e7463
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696216B2

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