p-Hydrazinobenzenesulphonamide → Enflicoxib

HRID 1611860

반응식

HRID 1611860 반응식
[O-]CC.[Na+].[F:5][C:6]([F:20])([F:19])[C:7](=O)[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].[NH2:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][NH2:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23]>C(O)C>[NH2:21][S:22]([C:25]1[CH:26]=[CH:27][C:28]([N:31]2[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])[CH2:8][C:7]([C:6]([F:20])([F:19])[F:5])=[N:32]2)=[CH:29][CH:30]=1)(=[O:24])=[O:23]

참가 물질

5

반응물 3

HCID 78105p-HydrazinobenzenesulphonamideHCID 2723922Sodium ethoxideHCID 69533569HCID 69533569, 화합물

생성물 1

HCID 9953093Enflicoxib수율 65%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

In a flask with an inert atmosphere sodium ethoxide (0.53 g, 7.72 mmoles) is dissolved in 45 ml of ethanol. 1,1,1-trifluoro-4-(2,4-difluorophenyl)-3-butene-2-one (prepared according to method E-1) (0.913 g, 3.86 mmoles) and 4-(aminosulphonyl)phenylhydrazine chlorohydrate (0.87 g, 3.87 mmoles) are added and the mixture was refluxed for 16 hours. The mixture was cooled, evaporated to dryness, cold water added, and the mixture acidified by adding acetic acid and the precipitated solid filtered. This solid was redissolved in ether, treated with active C, filtered and the solvent eliminated with a rotavapor. The resulting residue was crystallised from ethyl ether-petrol ether (50:50) to give 1-(4-aminosulphonylphenyl)-5-(2,4-difluorophenyl)-4,5-dihydro-3-trifluoromethyl-1H-pyrazole (1.02 g, yield: 65%) in the form of a solid m.p.=160-2° C.

후처리

  1. temperaturethe mixture was refluxed for 16 hours
  2. temperatureThe mixture was cooled
  3. customevaporated to dryness, cold water
  4. additionadded
  5. additionby adding acetic acid
  6. filtrationthe precipitated solid filtered
  7. dissolutionThis solid was redissolved in ether
  8. additiontreated with active C
  9. filtrationfiltered
  10. customThe resulting residue was crystallised from ethyl ether-petrol ether (50:50)

출처 및 근거

ORD 기록
ord-35b3b07460ee4250b3e32f0a0adbd8ca
출처 데이터셋
uspto-grants-2006_01
특허 번호
USRE038963E1

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