Preparation of an imine compound, useful as a raw material in the preparation of asymmetrical diimine compound, comprises reacting a carbonyl compound with a primary amine compound

摘要

Preparation of an imine compound (I) comprises reacting a carbonyl compound (II) with a primary amine compound (a). Preparation of an imine compound of formula (I) comprises reacting a carbonyl compound of formula (II) with a primary amine compound (a) of formula (G-NH 2). A 1>Cl, Br or I; either R 1>H, 1-22C-alkyl, 2-22C-alkenyl, 6-22C-aryl, arylalkyl with 1-10C atoms of alkyl and 6-20C atom of aryl, or 5-7 membered heterocycle containing at least one of N, P, O or S, where the organic residues are substituted by halo, NR 1>1>2, OR 1>1>or SiR 1>2>3; and R 3>-R 5>H, 1-22C-alkyl, 2-22C-alkenyl, 6-22C-aryl, arylalkyl with 1-10C atom of alkyl and 6-20C atoms of aryl, NR 1>1>2, OR 1>1>, halo, SiR 1>2>3or 5-7 membered heterocycle containing at least an atom of N, P, O or S (all optionally substituted by halo, NR 1>1>2, OR 1>1>or SiR 1>2>3); or R 1>+R 3>5-7 membered ring; or 2R 3>-R 5>5-7 membered ring, preferably heterocyclic ring containing N, P, O or S; either R 1>1>H, 1-22C-alkyl, 2-22C-alkenyl, 6-22C-aryl, arylalkyl with 1-10C atoms of alkyl and 6-20C atoms of aryl or SiR 1>2>3(all optionally substituted by halo); or 2R 1>1>5 or 6 membered ring; either R 1>2>H, 1-22C-alkyl, 2-22C-alkenyl, 6-22C-aryl or arylalkyl with 1-10C atoms of alkyl and 6-20C atoms of aryl; or 2R 1>2>5 or 6 membered ring; G : 1-22C-alkyl, 2-22C-alkenyl, 6-40C-aryl, arylalkyl with 1-10C atoms of alkyl and 6-20C atoms of aryl, NR 1>1>2, SiR 1>2>3or 5-7 membered heterocycle containing at least an atom of N, P, O or S (all optionally substituted by halo, NR 1>1>2, OR 1>1>or SiR 1>2>3); E 1>-E 3>C, N or P; and u : 0 (when E 1>-E 3>is N or P) or 1 (when E 1>-E 3>is C). Independent claims are included for: (1) the imine compound (I); and (2) a method for the preparation of an imine compound of formula (IV) comprising reacting (I) with a metal alkyl compound of formula (M1aR1a(X1a) n), and subsequently reacting the obtained product with a carbonyl compound of formula (R3a-C(O)X2a). Either R 2>R 1>; or 2(R 1>R 2>)+R 3>-R 5>5-7 membered ring; M1a : Li (preferred), Na, K, Mg, Ca, Sr or Ba; X1a : 1-22C-alkyl, 2-22C-alkenyl, 6-22C-aryl, arylalkyl with 1-10C atoms of alkyl and 6-20C atoms of aryl, F, Cl, Br, I, H, NR2a 2, OR2a, SR2a, SO 3R2a, OC(O)R2a, CN or SCN (all optionally substituted by halo); R1a, R2a : 1-22C-alkyl, 2-22C-alkenyl, 6-22C-aryl or arylalkyl with 1-10C of alkyl and 6-20C of aryl (all optionally substituted by halo); n : 0 (when M1a is Li, Na or K) or 1 (when M1a is Mg, Ca, Sr or Ba); X2a : F, Cl, Br, I, OM3a, NR4a 2, OR4a, SR4a or OC(O)R4a (all optionally substituted by halo); R3a : H, 1-22C-alkyl, 2-22C-alkenyl, 6-22C-aryl, arylalkyl with 1-10C of alkyl and 6-20C of aryl or SiR4A 3(all optionally substituted by halo); either R4a : 1-22C-alkyl, 2-22C-alkenyl, 6-22C-aryl or arylalkyl with 1-10C of alkyl and 6-20C of aryl; or 2R4a : 5 or 6 membered ring; and M2a : Li, Na or K. [Image] [Image].