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4-Toluenesulfonyl chloride → 6,6-diphenyl-1-(4-toluenesulphonyl)-6,7-dihydro-1H-indazol-3-carboxylic acid

HRID 1243836
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HRID 1243836 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]1([C:18]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:26][C:25]3[NH:24][N:23]=[C:22]([C:27]([OH:29])=[O:28])[C:21]=3[CH:20]=[CH:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)C.O.[OH-].[Na+]>[C:30]1([C:18]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:26][C:25]3[N:24]([S:7]([C:4]4[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=4)(=[O:9])=[O:8])[N:23]=[C:22]([C:27]([OH:29])=[O:28])[C:21]=3[CH:20]=[CH:19]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
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참가 물질

6

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 219286736,6-diphenyl-6,7-dihydro-1H-indazole-3-carboxylic acid

생성물 1

HCID 219291026,6-diphenyl-1-(4-toluenesulphonyl)-6,7-dihydro-1H-indazol-3-carboxylic acid수율 63.2%

시약·촉매·용매 3

HCID 962Water용매2회HCID 3283Diethyl Ether용매
HCID 14798
Sodium Hydroxide
용매

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온도
20 °C

실험 절차

A solution of 1 g of p-toluenesulphonyl chloride in 10 cm3 of diethyl ether is added, at a temperature in the region of 20° C., to a solution of 1 g of 6,6-diphenyl-6,7-dihydro-1H-indazol-3-carboxylic acid in 10 cm3 of water and 10 cm3 of a normal aqueous sodium hydroxide solution. The reaction mixture, which sets to a solid after about ten minutes of vigorous stirring, is diluted with 10 cm3 of water. After stirring for about eighteen hours at a temperature in the region of 20° C., the reaction mixture is filtered. The solid is washed with three times 20 cm3 of water and then suspended in 20 cm3 of water. 10 cm3 of a normal aqueous hydrochloric acid solution are added. The mixture is extracted with three times 50 cm3 of ethyl acetate. The combined organic phases are successively washed with three times 70 cm3 of water and once 70 cm3 of saturated aqueous sodium chloride solution and then dried over magnesium sulphate, filtered and concentrated under reduced pressure (13 kPa). The residue is purified by flash chromatography on a column of silica [eluent: dichloromethane/methanol (95/5 by volume)]. 0.94 g of 6,6-diphenyl-1-(4-toluenesulphonyl)-6,7-dihydro-1H-indazol-3-carboxylic acid is thus obtained in the form of a solid, the characteristics of which are as follows:

후처리

  1. waitThe reaction mixture, which sets to a solid after about ten minutes of vigorous stirring
  2. filtrationthe reaction mixture is filtered
  3. washThe solid is washed with three times 20 cm3 of water
  4. addition10 cm3 of a normal aqueous hydrochloric acid solution are added
  5. extractionThe mixture is extracted with three times 50 cm3 of ethyl acetate
  6. washThe combined organic phases are successively washed with three times 70 cm3 of water and once 70 cm3 of saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure (13 kPa)
  10. customThe residue is purified by flash chromatography on a column of silica [eluent: dichloromethane/methanol (95/5 by volume)]

출처 및 근거

ORD 기록
ord-bf7deb67199b468cb630d1e5704be87f
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07119115B2

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