Reaction #460374
ord-826ffedaef924ab8aa8bbfd7cb3d4210
Reaction equation
Reactants
Reagents
Solvents
Conditions
Workup
- 1Temperatureas heat
Procedure
N-[2-(2-hydroxyethyl)aminoethyl]octadecanamide and N-[2-(2-hydroxyethyl)aminoethyl]pentanamide have been obtained as hydrolysis products from the corresponding imidazolines by Harnsberger and Riebsomer, J. Hetero. Chem. 1, 188 (1964); Gabriel, J. Amer. Oil Chem. Soc., 61, 965 (1984), has described the formation of N-(2-aminoethyl)-N-(2-hydroxyethyl)dodecanamide and N-[2-(2-hydroxyethyl)aminoethyl]dodecanamide as kinetically and thermodynamically controlled products respectively from reaction of N-(2-aminoethyl)aminoethanol and methyl laurate in the presence of catalytic amount of sodium methoxide; Horibatake et al., Jpn. Kokai Tokkyo Koho JP 62,132,946, 16 Jun 1987; C.A. 108, 22881p (1988) claim acylaminoalkyl aminoalkanols, for example, N-[2-(2-hydroxy- ethyl)aminoethyl]dodecanamide, as antistatic agents for synthetic resins; Higuchi and Takahashi, Jpn. Kokai Tokkyo Koho JP 62 57,491, 13 Mar. 1987; C.A. 107, 178711y (1987) claim N-[2-(2-hydroxyethyl) aminoethyl]dodecanamide as being essential in a detergent composition useful for cleaning machines; Moriguchi, Jpn. Kokai Tokkyo Koho JP 62,104,842, 15 May 1987; C.A. 107, 177783m (1987) mentions compositions containing acylaminoalkyleneamines and aminoalcohols as antitack agents for unvulcanized rubbers; Higuchi and Takahashi, Jpn. Kokai Tokkyo Koho JP 61,114,726, 02 Jun 1986; C.A. 105, 155513e (1986) mention the use of N-[2-(2-hydroxyethyl) aminoethyl]dodecanamide and octadec-9-enamide and N-(2-aminoethyl)-N-(2-hydroxyethyl)dodecanamide as emulsifying agents for stable emulsions; Moriguchi, Jpn. Kokai Tokyo Koho JP 71 09,939, 13 Mar 1971; C.A. 76, 60500s (1972) describe the use of N-[2-(2-Hydroxyethyl)aminoethyl]dodecanamide and octadecanamide as heat and water resistant antistatic agents; N-2-aminoethylamides of lower carboxylic acids have been reported by Rosenmund, U.S. Pat. No. 1,926,015 (Sep. 5, 1933); dodecanoic and tetradecanoic acid derivatives (m.p. 51°-2° C. and 62° C.) have been synthesized by Weiner, U.S. Pat. No. 2,387,201 (Oct. 16, 1945) and the latter (m.p. 150°-152° C.) by Kyrides, U.S. Pat. No. 2,399,601 (Apr. 30, 1946), but purity of these compounds is questionable based on the discrepancy in the reported melting points; Harnsberger and Riebsomer have isolated N-[2-(2-hydroxyethyl)aminoethyl]octadecanamide and pentanamide as hydrolysis products from the corresponding imidazolines.