Sodium Bicarbonate → N-{4-[4-(4-Nitropyrid-2-yl)piperazin-1-yl]phenyl}methanesulphonamide

HRID 2232404노트

반응식

HRID 2232404 반응식
Cl.[N:2]1([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][N:21]=1.C(=O)(O)[O-].[Na+]>C(O)CCC>[N+:26]([C:24]1[CH:23]=[CH:22][N:21]=[C:20]([N:5]2[CH2:6][CH2:7][N:2]([C:8]3[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:12][CH:13]=3)[CH2:3][CH2:4]2)[CH:25]=1)([O-:28])=[O:27]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 7351522-Chloro-4-nitropyridineHCID 18759927N-[4-(piperazin-1-yl)phenyl]methanesulfonamide hydrochloride

생성물 1

HCID 21283530N-{4-[4-(4-Nitropyrid-2-yl)piperazin-1-yl]phenyl}methanesulphonamide

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A mixture of the product of (iii) above (1.46 g), 2-chloro-4-nitropyridine (0.79 g) and sodium bicarbonate (1.26 g) in n-butanol (30 ml) were heated under reflux with stirring for 24 hours and then cooled and filtered. The solid was washed with methanol and the combined filtrate and washings were evaporated to give a gum that was chromatographed on silica gel. Elution with dichloromethane, gradually increasing the polarity to dichloromethane/methanol (4:1) gave a mixture of the desired product, together with some N-{4-[4-(2-chloropyrid-4-yl)piperazin-1-yl]phenyl}methanesulphonamide biproduct, as a solid. The solid was crystallised four times from methanol to give pure N-{4-[4-(4-nitropyrid-2-yl)piperazin-1-yl]phenyl}methanesulphonamide (0.36 g), m.p. 182°-183° C. Found: C,50.90; H,5.07; N,18.51. C16H19N5O4S requires: C,50.91; H,5.07; N,18.56%.

후처리

  1. temperaturewere heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe solid was washed with methanol
  6. customthe combined filtrate and washings were evaporated
  7. customto give a gum that
  8. customwas chromatographed on silica gel
  9. washElution with dichloromethane
  10. temperaturegradually increasing the polarity to dichloromethane/methanol (4:1)
  11. customgave

출처 및 근거

ORD 기록
ord-1b3324e54c4e494ebe4ba925457e714b
출처 데이터셋
uspto-grants-1988_11
특허 번호
US04788196

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