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Hydrochloric Acid → N-[3-(2-aminophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide

HRID 1452876
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HRID 1452876 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29]([CH3:32])(=[O:31])=[O:30])(=[O:22])=[O:21])[CH:17]=2)[NH:12][N:11]=1)([O-])=O.C(O)C.Cl>[Fe].O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29]([CH3:32])(=[O:31])=[O:30])(=[O:22])=[O:21])[CH:17]=2)[NH:12][N:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 22567362N-[3-(2-nitrophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide

생성물 1

HCID 22567188N-[3-(2-aminophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide수율 15.3%

시약·촉매·용매 2

HCID 23925Iron촉매
HCID 962
Water
용매

실험 절차

N-[3-(2-Aminophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide can be obtained in the following way: 59 mg of powdered iron are added in small fractions to a solution, at reflux, of 280 mg of N-[3-(2-nitrophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide, 10 ml of ethanol, 82 μl of distilled water and 51 μl of 12 N hydrochloric acid, and the reaction medium is then brought to reflux for 3 hours. After returning to a temperature in the region of 20° C., the suspension is filtered, and washed with ethanol. The filtrate is diluted with water and brought to a pH in the region of 10 with a 1 N sodium hydroxide solution. The filtrate is extracted with ethyl acetate and the remaining insoluble material is removed by filtration. The organic phase is washed with distilled water, dried with magnesium sulfate, treated with 3S black, filtered and concentrated to dryness under reduced pressure. The foam thus obtained is triturated with diisopropyl ether, filtered and dried. 40 mg of N-[3-(2-aminophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide are thus obtained in the form of a white amorphous solid solvated with 1 mol of diisopropyl ether (analysis C20H18N4O4S2C6H14O % calculated C, 57.33; H, 5.92; N, 10.29; O, 14.69; S, 11.77. % found C, 57.41; H, 5.96; N, 10.01; S, 11.26).

후처리

  1. temperatureto reflux for 3 hours
  2. customAfter returning to a temperature in the region of 20° C.
  3. filtrationthe suspension is filtered
  4. washwashed with ethanol
  5. additionThe filtrate is diluted with water
  6. extractionThe filtrate is extracted with ethyl acetate
  7. customthe remaining insoluble material is removed by filtration
  8. washThe organic phase is washed with distilled water
  9. dry with materialdried with magnesium sulfate
  10. additiontreated with 3S black
  11. filtrationfiltered
  12. concentrationconcentrated to dryness under reduced pressure
  13. customThe foam thus obtained
  14. customis triturated with diisopropyl ether
  15. filtrationfiltered
  16. customdried

출처 및 근거

ORD 기록
ord-70896004c7954b0cba7f4b82969e9583
출처 데이터셋
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07473701B2

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