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

HRID 1874511

반응식

HRID 1874511 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][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N+:24]([C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=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)([O-:26])=[O:25]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 98231-Fluoro-3-nitrobenzeneHCID 11430Potassium CarbonateHCID 57980821HCID 57980821, 화합물

생성물 1

HCID 57749256N-[6-(3-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide수율 37%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
150 °C

실험 절차

A mixture of N-(6-hydroxy-1,3-benzothiazol-2-yl)cyclopropanecarboxamide (3.54 g, 15.1 mmol), 1-fluoro-3-nitrobenzene (2.24 g, 15.9 mmol), potassium carbonate (6.26 g, 45.3 mmol) and N,N-dimethylformamide (30 mL) was stirred at 150° C. for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was collected by filtration and washed with ethyl acetate-hexane to give the title compound (1.82 g, 37%) as a white solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. filtrationthe residue was collected by filtration
  7. washwashed with ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-30087a2cdad74e8aadc57da2389951e5
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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