Accession Number:

AD0730880

Title:

Reaction of trans-2-Acylaminocyclanols with Thionyl Chloride,

Descriptive Note:

Corporate Author:

DEFENCE RESEARCH ESTABLISHMENT OTTAWA (ONTARIO)

Report Date:

1970-12-23

Pagination or Media Count:

11.0

Abstract:

Trans-2-Acetamidocyclohexanol n 2, R CH3 on addition to thionyl chloride in chloroform at 0C was converted rapidly and quantitatively to D,L-2-methyl-4,5-cis-cyclohexanooxazoline hydrochloride n 2, R CH3 judging from shifts in the methyl proton resonances of the n.m.r. spectra of the amide and the reaction solution. The intermediate chlorosulfinate was estimated to have a half-life of less than 2.25 min. The oxazoline salt was isolated in 98 yield by sublimation of the crude product in vacuo and was identified by its i.r. and n.m.r. spectra and by its facile and almost quantitative hydrolysis to cis-2-aminocyclohexanol hydrochloride. It was shown that the trans-2-acetamidocyclanols are the preferred starting materials for conversion to cis-2-aminocyclanol derivatives by the thionyl chloride inversion reaction. The oxazoline bases n 1, R CH3, C6H4-pNO2 and n 2, R CH3, C6H4-pNO2 were readily obtained in high yield from the corresponding salts and differences in the i.r. and n.m.r. spectral characteristics of the salts and bases are reported. Author

Subject Categories:

  • Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE