N,N'-Bis(2-chloroethyl)-N-nitrosourea → 1,3-Bis(2-chloroethyl)urea

HRID 436912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 436912
[CH2:1]([NH:4][C:5]([N:7](N=O)[CH2:8][CH2:9][Cl:10])=[O:6])[CH2:2][Cl:3].CCCCCC>C1C=CC=CC=1>[Cl:3][CH2:2][CH2:1][NH:4][C:5]([NH:7][CH2:8][CH2:9][Cl:10])=[O:6]

Komponenten

4

Edukt 2

HCID 2578N,N'-Bis(2-chloroethyl)-N-nitrosoureaHCID 8058Hexane

Produkt 1

HCID 957911,3-Bis(2-chloroethyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A suspension of 1.11 mmole (0.205 g) of 1,3-bis(2-chloroethyl)urea in 8 ml methylene dichloride at -10° C. was saturated with dinitrogen trioxide in 20% excess of theoretical. The heterogeneous mixture gradually changed to a green homogeneous solution. The methylene dichloride was evaporated, and the residue was extracted with 3× 10 ml hexane. Evaporation of the hexane gave 0.1773 g of oil which was the crude BCNU (NSC 409962). The hexane insoluble portion, 0.0649 g, when treated with benzene, gave 0.020 g of 1,3-bis(2-chloroethyl)urea which was benzene insoluble. The benzene solubles were processed through a silica column (1× 10 cm) and 0.0245 g of crude BCNU was obtained. The combined fractions of crude product amounted to 0.2018 g (85.1%).

Quellen und Nachweise

ORD-Eintrag
ord-0f3548f5f5a245ccb80443ca4a60f70d
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04028410

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