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Sulfuric Acid → HCID 59632294, 화합물

HRID 2369059
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HRID 2369059 반응식
[OH:1]S(O)(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:17]([C:18]2[S:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:24]=3)=[CH:21][CH:22]=2)=[CH:16][C:15]([CH2:33][C:34]#N)=[N:14]1.[C:36]([O-])([O-])=[O:37].[Na+].[Na+]>CO.O.O>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:17]([C:18]2[S:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:24]=3)=[CH:21][CH:22]=2)=[CH:16][C:15]([CH2:33][C:34]([O:37][CH3:36])=[O:1])=[N:14]1
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참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 59633179HCID 59633179, 화합물

생성물 1

HCID 59632294HCID 59632294, 화합물수율 82%

시약·촉매·용매 2

HCID 962Water용매HCID 22242641Methanol--water (1/1)용매

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온도
90 °C

실험 절차

Concentrated H2SO4 (4 mL) was added dropwise at 0° C. to a stirred solution of the [1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]acetonitrile (148 mg, 0.33 mmol) in a mixture of MeOH—H2O (10:1, 11 mL), and the resulting mixture was stirred at 90° C. overnight. The mixture was diluted with cold water, then basified with Na2CO3 solid, extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-40% 20% MeOH/DCM) to afford the title compound as a white solid (131 mg, 82%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.83-7.81 (m, 1H), 7.73-7.71 (m, 1H), 7.57-7.41 (m, 5H), 7.20 (d, 1H), 6.75 (d, 1H), 6.69 9s, 1H), 3.82 9s, 2H), 3.79 (s, 3H), 3.08 (s, 3H). MS(ES): 487 [M+H]+.

후처리

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography (0-40% 20% MeOH/DCM)

출처 및 근거

ORD 기록
ord-bbe182e68e9a4c898789c114db40f536
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08703805B2

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