Sodium amide → HCID 54442006, Verbindung

HRID 361310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 361310
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.I[CH2:10][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14].[NH2-].[Na+].BrN1C(=O)CCC1=O.[CH2:29]([O:31][P:32]([O:36]CC)[O:33][CH2:34][CH3:35])[CH3:30]>C(Cl)(Cl)(Cl)Cl.O1CCCC1>[CH2:13]([O:12][P:11]([CH:10]([NH:8][C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[P:32](=[O:36])([O:33][CH2:34][CH3:35])[O:31][CH2:29][CH3:30])(=[O:18])[O:15][CH2:16][CH3:17])[CH3:14]

Komponenten

8

Edukt 5

HCID 24533Sodium amideHCID 31215Triethyl phosphiteHCID 67184N-bromobutanimideHCID 793055-Amino-2-chloropyridineHCID 82616Diethyl (iodomethyl)phosphonate

Produkt 1

HCID 54442006HCID 54442006, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943Carbon TetrachlorideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Chloro-3-aminopyridine was alkylated with diethyl iodomethylphosphonate, sodium amide as base, with known methods. The obtained 6-chloro-3-pyridinylamino-methylphosphonic acid diethylester (0.5 mol) and N-bromosuccinimid (0.5 mol) in anhydrous carbontetrachloride is irradiated 2 hours with a 200 W lamp. The solid is filtered off, washed with carbontetrachloride and the solution is concentrated in vacuo. The obtained 6-chloro-3-pyridinylamino(bromomethyl)-phosphonic acid diethylester (0.1 mol) is warmed in tetrahydrofuran with triethylphosphite (0.1 mol) in 50° C. for 4 hours. The reaction mixture is concentrated in vacuo. The product is purified chromatographically (eluent dichloromethane: methanol 9:1). Yield 5.1 g.

Aufarbeitung

  1. filtrationThe solid is filtered off
  2. washwashed with carbontetrachloride
  3. concentrationthe solution is concentrated in vacuo
  4. concentrationThe reaction mixture is concentrated in vacuo
  5. customThe product is purified chromatographically (eluent dichloromethane: methanol 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-5fd55d8448eb42f3a163a04a6d76f5db
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866556

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