Preparation of n-methoxy-n-methylurethanes

Details Preparation of n-methoxy-n-methylurethanes Preparation of n-methoxy-n-methylurethanes

1983-04-14

1984-09-04

Shippen, Michael L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C07C125065

Patent

active

044698844

ABSTRACT:
N-Methoxy-N-methylurethanes are prepared by a process in which first (1) hydroxylamine is converted with an alkyl chloroformate to the corresponding N-hydroxyurethane, then (2) this product is reacted with a methylating agent to give the N-methoxy-N-methylurethane, and finally (3) the N-methoxy-N-methylurethane is isolated. In this process, first, (1) while maintaining a certain temperature and a certain pH, (1.1) an aqueous solution of an inorganic hydroxylammonium salt is mixed thoroughly with (1.2) an equimolar amount of an alkyl chloroformate, then (2) while maintaining a certain temperature and a certain pH, (2.1) a mixture comprising (2.1.1) the reaction mixture obtained as described in (1), (2.1.2) a water-insoluble organic solvent and (2.1.3) a phase-transfer catalyst is mixed thoroughly with (2.2) a water-insoluble methylating agent which is soluble in the solvent under (2.1.2), and the resulting mixture is kept at a certain temperature for a certain time, and finally (3) any methylating agent still present in the reaction mixture obtained as described in (2) is destroyed, the non-aqueous liquid phase is separated off from the mixture thus treated, and the N-methoxy-N-methylurethane is isolated from this phase by stripping off the solvent. A relatively pure product is obtained in high yield.

REFERENCES:
Sandler, "Organic Functional Group Preparations, vol. III, pp. 321-327, 339-344, (1972).
A. T. Fuller and H. King, J. Chem. Soc. (London), 1947, 963.
R. T. Major and E. E. Fleck, Am. Soc. 50, (1928), 1479.

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