N-acylation of oxazolidines

Details N-acylation of oxazolidines N-acylation of oxazolidines

1976-01-07

1977-07-26

Daus, Donald G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260691, C07D26304

Patent

active

040382842

ABSTRACT:
N-substituted oxazolidines having the formula ##STR1## in which R is C.sub.1 -C.sub.10 haloalkyl, C.sub.1 -C.sub.10 alkyl or lower alkylthio; and R.sub.1 and R.sub.2 are independently hydrogen, C.sub.1 -C.sub.12 alkyl, lower alkoxyalkyl or lower alkylol; and R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently hydrogen, lower alkyl, lower alkoxyalkyl or lower alkylol are prepared by reacting an oxazolidine with an acid chloride or analogous compound in the presence of a hydrogen chloride acceptor and water. The process is characterized by minimization of by-product formation.
In a preferred embodiment, the oxazolidine is prepared by reaction of an alkanolamine with an aldehyde or ketone and the water of reaction is retained in the system.

REFERENCES:
patent: 3707541 (1972-12-01), Lajiness
Sheehan et al., J. Amer. Chem. Soc. 71 1856 (1949).
Warnhoff et al., Chem. Benchte 100, 2122 (1967).
Kent et al., Organic Syn. Collective vol. III, p. 490 (1955).
Carter et al., Organic Syn. Collective vol. III, p. 167 (1955).
Bergman, Chemical Reviews 53, 310-317, 321-324.

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