Ethyl methallylic amine

Ethyl mercapto ethyl thiocyanate demeton-S-ethyl, demeton-S-methyl, demeton-S-methyl sulfone, oxydemeton Ethyl methallyl amine ethalfluralin... 

The reaction of ethyl methallylic amine under HAM conditions in common organic solvents may lead via intramolecular hydrocarboxylation to the corresponding lactam 2 as a result of the fast nucleophilic attack of the nitrogen atom at the carbonyl group in the intermediate rhodium-acyl complex (Scheme 5.98) [35a, 82]. This path could be suppressed by running the reaction in supercritical... 

Scheme 5.98 Pathways in the hydroaminomethylation of ethyl methallylic amine.

A pyrrol-fused azepine was formed under HAM conditions of Af-ethyl-AT-methallyl amine (Scheme 5.114) [83]. Individual steps are intramolecular HAM, Mannich-type aldol condensation to form the bicyclic skeleton, and final... 

Scheme 5.114 Formation of a fused azepine by hydroaminomethylation of N-ethyl-N-methallylic amine.

A mixture of methyl 2-(p-aminophenyl)propionate (44.75 g), methallyl chloride (34 g) and pyridine (30 ml) in isopropanol (400 ml) is boiled during 30 hours. The solvent is removed in vacuo and the residue is taken up into water and ether. After separation, the organic phase is washed repeatedly with water, after which it is dried and concentrated in vacuo. The resulting oil is fractionally distilled in vacuo (0.1 mm Hg 5 g of oil essentially consisting of methyl 2-(p-aminophenyl)propionate are collected at 115°-120°C 30 g of oil consisting of a mixture of mono- (80%) and disubstituted (20%) amines is collected at 128°-130°C. This oil is used to prepare the hydrochloride, which is recrystallized from ethyl acetate, to give white crystals (22.7 g) melting at... 

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