Isopropyl chloroformate → HCID 178459833, Verbindung

HRID 506602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506602
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([OH:3])=[O:2].[NH2:12][C:13]1[C:18]([NH2:19])=[CH:17][C:16]([N+:20]([O-])=O)=[CH:15][N:14]=1.Cl[C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25].[OH-].[Na+]>CN1C(=O)CCC1.O>[CH:27]([O:26][C:24]([NH:20][C:16]1[CH:17]=[C:18]2[N:19]=[C:7]([C:6]3[CH:5]=[C:4]([CH:11]=[CH:10][CH:9]=3)[C:1]([OH:3])=[O:2])[NH:12][C:13]2=[N:14][CH:15]=1)=[O:25])([CH3:29])[CH3:28]

Komponenten

7

Edukt 4

HCID 7917Isopropyl chloroformateHCID 120773-CarboxybenzaldehydeHCID 14798Sodium HydroxideHCID 34801515-Nitropyridine-2,3-diamine

Produkt 1

HCID 178459833HCID 178459833, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

was prepared starting from 3-carboxybenzaldehyde and 2,3-diamino-5-nitropyridine as described for 10-1. In the final step, after reacting with isopropyl chloroformate in NMP, the reaction mixture was treated with 100 mg sodium hydroxide and 1 ml water for 1 hr at room temperature. The crude product was precipitated by addition of 30 ml water and filtered off. It was further purified by dissolving in 50 ml aqueous sodium carbonate solution and washing with dichloromethane. The carbonate solution was acidified to pH 2-3 by addition acetic acid and HCl, and extracted with dichloromethane. The dichloromethane phase was evaporated to give 61 mg of the title product.

Aufarbeitung

  1. customwas prepared
  2. customThe crude product was precipitated by addition of 30 ml water
  3. filtrationfiltered off
  4. customIt was further purified
  5. dissolutionby dissolving in 50 ml aqueous sodium carbonate solution
  6. washwashing with dichloromethane
  7. additionThe carbonate solution was acidified to pH 2-3 by addition acetic acid and HCl
  8. extractionextracted with dichloromethane
  9. customThe dichloromethane phase was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-abbb1f9db501497e9bd603e6d6612106
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786113B2

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