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

HRID 2232404ノート

反応式

HRID 2232404 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-1b3324e54c4e494ebe4ba925457e714b
出典データセット
uspto-grants-1988_11
特許番号
US04788196

反応ノート

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