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Sodium Hydroxide → 5-n-Butyl-4-(4-carboxybenzyl)-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

HRID 36240
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HRID 36240 반응식
[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([O:30]C)=[O:29])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C1COCC1.CO>[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:17])[F:18])[N:9]=1)[CH2:2][CH2:3][CH3:4]
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참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 199394365-n-Butyl-2,4-dihydro-4-[4-(methoxycarbonyl)benzyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

생성물 1

HCID 199394615-n-Butyl-4-(4-carboxybenzyl)-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one수율 96%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran
용매

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온도
60 °C

실험 절차

A solution of 25 mg (0.0577 mmole) of 5-n-butyl-2,4-dihydro-4-[4-(methoxycarbonyl)benzyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 26) in 0.25 mL of THF was treated with 0.25 mL of 1N sodium hydroxide in methanol, and the resulting solution was stirred overnight at 60° C. Volatiles were removed by evaporation, and the residue was taken up in 1 mL of methanol and acidified to pH 1.5 by addition of 1N HCl in methanol. The mixture was concentrated to dryness. The residue was leached with chloroform. The CHCl3 solution was dried over anhydrous sodium sulfate, filtered through Celite, and concentrated in vacuo to give 23 mg (96%) of the title compound as a colorless, glassy solid; homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 420 (M+1)+.

후처리

  1. customVolatiles were removed by evaporation
  2. additionacidified to pH 1.5 by addition of 1N HCl in methanol
  3. concentrationThe mixture was concentrated to dryness
  4. dry with materialThe CHCl3 solution was dried over anhydrous sodium sulfate
  5. filtrationfiltered through Celite
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ec6e9dc321a442e3abca84b4aab65d41
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05411980

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