Process for the manufacture of .beta.-isobutyrylaminocrotonic ac

Details Process for the manufacture of .beta.-isobutyrylaminocrotonic ac Process for the manufacture of .beta.-isobutyrylaminocrotonic ac

1979-12-03

1980-12-30

Demers, Arthur P.

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

Organic compounds

Amino nitrogen containing

C07C 9716

Patent

active

042422760

ABSTRACT:
A process for the manufacture of .beta.-isobutyrylaminocrotonic acid amide by reacting .beta.-aminocrotonic acid amide with dimethylketene in the liquid or gaseous state without the application of external heat at temperatures in the range of from room temperature to 70.degree. C. The dispersion medium used is an organic solvent having a boiling point above 40.degree. C. that may contain up to 0.1 mole of water and 0.2 to 2 moles of a carboxylic acid having 1 to 4 carbon atoms per mole of .beta.-aminocrotonic acid amide. If the dimethylketene is added undiluted the reaction is carried out in the absence of oxygen and in the presence of a protective gas atmosphere. The .beta.-isobutyrylaminocrotonic acid amide is obtained in the form of two stereoisomers (Z- and E-forms), which differ as regards their melting point and their solubility in organic solvents. On heating to 40.degree. C., the E-form is converted into the Z-form.

REFERENCES:
patent: 3367947 (1968-02-01), Cornforth
patent: 3458573 (1969-07-01), Tieman
patent: 3459801 (1969-08-01), Beriger
patent: 3483252 (1969-12-01), Beriger
patent: 3703518 (1972-11-01), Inol et al.
patent: 4129596 (1978-12-01), Kunstle et al.
Kato et al., Tetrahedron 23 (1967) p. 2965-2971.

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