Process for the preparation of oxadiazolines

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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260562H, 568588, C07D27110

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active

041384040

ABSTRACT:
Oxadiazoline derivatives of the formula: ##STR1## WHEREIN R is alkyl of 1 through 4 carbon atoms, which are useful as intermediates in the synthesis of oxadiazoline derivatives of the formula: ##STR2## WHEREIN R is as defined above the R.sub.1 is alkyl of 1 through 4 carbon atoms, possessing useful herbicidal properties, are prepared by a new process which comprises reducing the nitro group in a 5-alkyl-3-(2-nitro-4-chlorophenyl)-1,3,4-oxadiazolin-2-one of the formula: ##STR3## wherein R is as defined above to a hydroxylamino group, treating the resulting 5-alkyl-3-(2-hydroxylamino-4-chlorophenyl)-1,3,4-oxadiazolin-2-one with concentrated sulphuric acid of density about 1.83 to produce the corresponding amino-phenol, and converting the amine group in the resulting 5-alkyl-3-(2-amino-4-chloro-5-hydroxyphenyl)-1,3,4-oxadiazolin-2 -one to a chlorine atom. The 5-alkyl-3-(2-hydroxylamino-4-chlorophenyl)-1,3,4-oxadiazolin-2-one intermediates are new compounds.

REFERENCES:
patent: 3846439 (1974-11-01), Boesch et al.
Morrison et al. -- Organic Chemistry -- Allyn & Bacon, Inc. -- 1959 -- pp. 570-571.
Smith, P. A. S. -- Open-Chain Nitrogen Compounds -- vol. 2 -- W. A. Benjamin, Inc. -- 1966 -- p. 15.
Bamberger -- Chem. Ber. 27, pp. 1347, 1349-1350, 1548, 1552 (1894).

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