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Water → N-[6-(2-fluoro-4-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

HRID 2095769
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HRID 2095769 반응식
[OH:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([CH:12]3[CH2:14][CH2:13]3)=[O:11])[S:8][C:4]=2[CH:3]=1.F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=1[F:27].C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[F:27][C:19]1[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=1[O:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([CH:12]3[CH2:13][CH2:14]3)=[O:11])[S:8][C:4]=2[CH:3]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 57980821N-(6-hydroxy-1,3-benzothiazol-2-yl)cyclopropanecarboxamide

생성물 1

HCID 58158566N-[6-(2-fluoro-4-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide수율 65.4%

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

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온도
50 °C

실험 절차

A suspension of N-(6-hydroxy-1,3-benzothiazol-2-yl)cyclopropanecarboxamide (1.17 g, 5.00 mmol), 1,2-difluoro-4-nitrobenzene (0.96 g, 6.00 mmol) and cesium carbonate (3.26 g, 10.0 mmol) in dimethyl sulfoxide (10 mL) was stirred at 50° C. for 5 hr. After cooling to room temperature, water was added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate/tetrahydrofuran. The organic layer was washed with water, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate and collected by filtration to give the title compound (1.22 g, 65%) as a pale-yellow solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted 3 times with ethyl acetate/tetrahydrofuran
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. washthe residue was washed with ethyl acetate
  8. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-7b69cda19e7343b3a69f07c8f4d67355
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08445509B2

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