Benzenamine, 3-chloro-, hydrochloride (1:1) → Chloride

HRID 1068939

Reaktionsgleichung

Reaktionsgleichung von HRID 1068939
[C:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:21]([C:22]#[N:23])=[C:20]([N:24](C)[CH3:25])[N:19](N=C)[N:18]=2)=[CH:12][CH:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[Cl:30][C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34]>C(O)C>[Cl-:30].[C:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:21]3[C:20](=[N:24][CH:25]=[N:23][C:22]=3[NH:34][C:33]3[CH:35]=[CH:36][CH:37]=[C:31]([Cl:30])[CH:32]=3)[NH:19][N:18]=2)=[CH:12][CH:11]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Komponenten

5

Edukt 2

HCID 67336Benzenamine, 3-chloro-, hydrochloride (1:1)HCID 696969723-[4-(N-Boc-aminomethyl)-phenylamino]-4-cyano-5-dimethylamino-methyleneamino-pyrazole

Produkt 2

HCID 312ChlorideHCID 178453074HCID 178453074, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 94 g (245.1 mmol) of 3-[4-(N-Boc-aminomethyl)-phenylamino]-4-cyano-5-dimethylamino-methyleneamino-pyrazole, 44.2 g (269.4 mmol) of 3-chloro-aniline hydrochloride [for preparation see: Justus Liebigs Ann. Chem. 176, 45 (1875)] and 1000 ml of ethanol is heated under reflux for 60 hours and then concentrated by evaporation in vacuo. The residue is dissolved in ethyl acetate, and the organic phase is washed with ice-cold 0.5N hydrochloric acid, water and brine, dried over sodium sulfate and concentrated by evaporation in vacuo. After recrystallization of the residue from ethyl acetate/hexane and from methanolimethylene chloride, 3-[4-(N-Boc-aminomethyl)-phenylamino]-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine is obtained; m.p. 196° C.; ESI-MS: (M−H)−=464.

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for 60 hours
  3. concentrationconcentrated by evaporation in vacuo
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washthe organic phase is washed with ice-cold 0.5N hydrochloric acid, water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated by evaporation in vacuo
  8. customAfter recrystallization of the residue from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-dc2811f085cf4f53acfd123559381d8f
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251911B1

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