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Dimethyl Sulfoxide → HCID 59633179, 화합물

HRID 2369058
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HRID 2369058 반응식
Br[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=3)=[CH:11][CH:12]=2)[N:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[N:4]=1.[C-:30]#[N:31].[Na+].CS(C)=O>O>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[N:5]1[C:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=3)=[CH:11][CH:12]=2)=[CH:7][C:3]([CH2:2][C:30]#[N:31])=[N:4]1
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참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 59632228HCID 59632228, 화합물

생성물 1

HCID 59633179HCID 59633179, 화합물수율 54.3%

시약·촉매·용매 1

HCID 962Water용매

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온도
100 °C

실험 절차

A mixture of the 3-bromomethyl-1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-thiophen-2-yl]-1H-pyrazole (720 mg, 1.42 mmol), NaCN (250 mg, 5.1 mmol), and DMSO (10 mL) was stirred in a sealed vial at 100° C. for 5 h, diluted with water, and extracted with EtOAc. The combined extracts were washed with water, brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-80% EtOAc/hexanes) to give the title compound as a white solid (350 mg, 54%). 1HNMR (CDCl3): δ 8.03 (d, 1H), 7.84 (m, 1H), 7.72 (m, 1H), 7.58-7.44 (m, 5H), 7.22 (d, 1H), 6.79 (d, 1H), 6.73 (s, 1H), 3.87 (s, 2H), 3.09 (s, 3H). MS(ES): 454 [M+H]+.

후처리

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography (0-80% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-922f428fa70c4db8a8752f90fe63d339
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08703805B2

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