Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1974-11-13
1977-06-07
Wyman, Daniel E.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
424322, C07C12715
Patent
active
040284107
ABSTRACT:
A method of producing 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU) by nitrosation of 1,3-bis(2-chloroethyl)-urea utilizing as a nitrosating agent dinitrogen trioxide (N.sub.2 O.sub.3) in molar excess of theoretical wherein the molar excess of N.sub.2 O.sub.3 ranges from 10-200% and preferably from 10-20%. The nitrosation reaction is conventionally carried out in the cold from 0.degree. C to -20.degree. C and a non-aqueous solvent is utilized. The preferred non-aqueous solvent is of the chlorinated variety; i.e., methylene dichloride. Other preferred solvents include related halogenated compounds such as ethylene dichloride, nitro-compounds such as nitromethane, acetonitrile, and simple ethers such as ethyl ether. Other less preferred but operable compounds include esters such as ethyl acetate, simple ketones such as acetones, and chloroform. Solvents to be avoided are olefins, unsaturated ethers and other unsaturated compounds, amines, malonate esters, acid anhydrides, and solvents which would interact with the reactant N.sub.2 O.sub.3 and the urea as well as the product nitrosourea.
REFERENCES:
patent: 3465025 (1969-09-01), Brownstein et al.
Johnston et al., J. Med. Chem., vol, 18, No. 1, 1975, pp. 104-106.
Montero et al., C. R. Acad. Sc. Paris, t. 279, Series C, 1974, pp. 809-811.
Ryan et al., CA 17: 1792-1793 (1923).
Sharp Donald E.
Yanko William H.
Ferris Thomas G.
Latker Norman J.
Roberts, Jr. John S.
The United States of America as represented by the Secretary of
Waltz Thomas A.
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