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Ethanol → 1-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acid

HRID 1257308
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HRID 1257308 반응식
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([CH2:14][N:15]3[CH:19]=[C:18]([C:20]([O:22]CC)=[O:21])[CH:17]=[N:16]3)[S:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.C(O)C.[OH-].[Na+]>O1CCCC1>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([CH2:14][N:15]3[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[CH:17]=[N:16]3)[S:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 66939193ethyl 1-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

생성물 1

HCID 442538511-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acid수율 67.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To the compound (4.80 g, 12.6 mmol) obtained in Example 1c were added ethanol (40 mL), tetrahydrofuran (10 mL) and 2N aqueous sodium hydroxide solution (12.6 mL, 25.2 mmol), and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with water, and washed with ether. The aqueous layer was acidified with 6N hydrochloric acid, extracted with ethyl acetate, washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (3.0 g, 67%) as colorless crystals.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with water
  3. washwashed with ether
  4. extractionextracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-a3489bb8b28440acb467230f7817596f
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08461348B2

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