2-Chloroethyl isocyanate → alpha-[N-(2-chloroethyl)ureido]benzylphosphonic acid diethyl ester

HRID 1285324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1285324
[CH2:1]([O:3][P:4]([CH:9](N)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[Cl:17][CH2:18][CH2:19][N:20]=[C:21]=[O:22].[NH2:23]P(=O)([O-])[O-]>C(Cl)(Cl)Cl>[CH2:6]([O:5][P:4]([CH:9]([N:20]([CH2:19][CH2:18][Cl:17])[C:21]([NH2:23])=[O:22])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Komponenten

5

Edukt 3

HCID 160352-Chloroethyl isocyanateHCID 211207Phosphoramidic acid, ion(2-)HCID 419299Diethyl amino(phenyl)methylphosphonate

Produkt 1

HCID 53798997alpha-[N-(2-chloroethyl)ureido]benzylphosphonic acid diethyl esterAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A solution of 0.05 mol of α-aminobenzylphosphonic acid diethyl ester in 30 ml of chloroform is cooled to 0° C. in an ice-bath and then a large excess (0.06 mol) of β-chloroethyl isocyanate is added. The temperature of the reaction is then maintained at 10° C. while continuing stirring until the reaction is complete. (Examination by thin layer chromatography is used to ascertain that the starting aminophosphonate has disappeared completely. After evaporation of the solvent under reduced pressure, the crystalline residue is taken up in ether and filtered, yielding 14.8 g of crystals. Yield: 85%; m.p.=82° C.

Aufarbeitung

  1. customAfter evaporation of the solvent under reduced pressure
  2. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-0cf852b59ea6435d8966c57c256c5a66
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04567169

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