1,2-Dimethylhydrazine dihydrochloride → 4-bromo-N-[4-chloro-2-(N,N'-dimethylhydrazinocarbonyl)-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxamide

HRID 2427076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2427076
Cl.Cl.[CH3:3][NH:4][NH:5][CH3:6].C(=O)([O-])[O-].[K+].[K+].[Br:13][C:14]1[CH:15]=[C:16]([C:26]2[O:31][C:30](=[O:32])[C:29]3[CH:33]=[C:34]([Cl:38])[CH:35]=[C:36]([CH3:37])[C:28]=3[N:27]=2)[N:17]([C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:18]=1>O.CN(C)C=O>[Br:13][C:14]1[CH:15]=[C:16]([C:26]([NH:27][C:28]2[C:36]([CH3:37])=[CH:35][C:34]([Cl:38])=[CH:33][C:29]=2[C:30]([N:4]([CH3:3])[NH:5][CH3:6])=[O:32])=[O:31])[N:17]([C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:18]=1

Komponenten

6

Edukt 3

HCID 93801,2-Dimethylhydrazine dihydrochlorideHCID 11430Potassium CarbonateHCID 668538312-[4-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrol-2-yl]-6-chloro-8-methyl-4H-3,1-benzoxazine-4-one

Produkt 1

HCID 577801874-bromo-N-[4-chloro-2-(N,N'-dimethylhydrazinocarbonyl)-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxamideAusbeute 23,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 0.29 g of N,N′-dimethylhydrazine dihydrochloride, 1 ml of water, 0.31 g of potassium carbonate and 10 ml of N,N-dimethylformamide was added 1.0 g of 2-[4-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrol-2-yl]-6-chloro-8-methyl-4H-3,1-benzoxazine-4-one. The resulting mixture was stirred at room temperature for 6 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate three times. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 0.26 g of 4-bromo-N-[4-chloro-2-(N,N′-dimethylhydrazinocarbonyl)-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxamide of the formula:

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-83a5744187864ad19f88759f49675a5b
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968573B2

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