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Benzyl Bromide → 2-Benzyl-5-butyl-4-[4-[(1-carboxy)(1-(2-chlorophenyl))methoxy]phenyl]methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 257847
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HRID 257847 반응식
[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([C:27]([O:29]C)=[O:28])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[CH:14][CH:13]=2)[C:7](=[O:10])[NH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C>[CH2:33]([N:8]1[C:7](=[O:10])[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([C:27]([OH:29])=[O:28])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[CH:14][CH:13]=2)[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 197818905-butyl-4-[4-[(1-carbomethoxy)(1-(2-chlorophenyl))methoxy]phenyl]methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

생성물 1

HCID 197818302-Benzyl-5-butyl-4-[4-[(1-carboxy)(1-(2-chlorophenyl))methoxy]phenyl]methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

A mixture of the above ester (Step G), sodium hydride (3 equivalents), and dry DMF is stirred under N2 at room temperature for 2 hours. Next, benzyl bromide (5 equivalents) is added, and stirring at room temperature is continued for an additional 1.5 hours or until TLC indicates complete reaction. The mixture is quenched by cautious addition of sufficient acetic acid to destroy the excess sodium hydride and then partitioned between ethyl acetate and H2O. The ethyl acetate phase is washed repeatedly with H2O, then dried (Na2SO4), filtered, and concentrated in vacuo. Chromatography of the residue on silica gel affords the title compound.

후처리

  1. stirringstirring at room temperature
  2. waitis continued for an additional 1.5 hours or until TLC
  3. customreaction
  4. customThe mixture is quenched by cautious addition of sufficient acetic acid
  5. customto destroy the excess sodium hydride
  6. custompartitioned between ethyl acetate and H2O
  7. washThe ethyl acetate phase is washed repeatedly with H2O
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9febca264e064b8892b66ae88c3afc2e
출처 데이터셋
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05264439

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