Dimethyl sebacate → N,N'-bis(4,4-dimethoxybutyl)sebacamide

HRID 1742118

Reaktionsgleichung

Reaktionsgleichung von HRID 1742118
[C:1]([O:15]C)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]C)=O.[CH3:17][O:18][CH:19]([O:24][CH3:25])[CH2:20][CH2:21][CH2:22][NH2:23]>C[O-].C[O-].C([Sn+2]CCCC)CCC>[CH3:17][O:18][CH:19]([O:24][CH3:25])[CH2:20][CH2:21][CH2:22][NH:23][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([NH:23][CH2:22][CH2:21][CH2:20][CH:19]([O:24][CH3:25])[O:18][CH3:17])=[O:15]

Komponenten

4

Edukt 2

HCID 7829Dimethyl sebacateHCID 54638031-Butanamine, 4,4-dimethoxy-

Produkt 1

HCID 18958118N,N'-bis(4,4-dimethoxybutyl)sebacamideAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 16049892Dibutyltin methoxideKatalysator

Versuchsvorschrift

Dimethyl sebacate (25.00 g, 0.1085 mol) was aminated with 30.63 g (0.230 mol) of 4,4-dimethoxybutylamine and 2.50 g (0.00847 mol) of dibutyl tin dimethoxide in 200 g of mixed xylenes according to the procedure used in Example 1. This procedure afforded 40.00 g (0.0925 mol, 85.2% isolated yield) of the desired N,N'-bis(4,4-dimethoxybutyl)sebacamide after recrystallization from mixed xylenes, mp 83.5°-85.5° C.; IR (KBr) 1640 (C=O), 1540, 1190, 1135, 1040 cm-1 ; 1H NMR (CDCl3 ; 300 MHz) δ1.13 (br s, 8H, --CH2 --), 1.35-1.58 (m, 12H, --CH2.00 (t, 4H, J=7.6 Hz, CO--CH2 --), 3.08 (m, 4H, --NH2CH2 --), 3.16 (s 12H, --OCH3), 4.20 (t, 2H, J=5.1 Hz, CH2CH--), 6.38 (t, 2H, J=5.4 Hz, --NH--CH2 --), 13C NMR (CDCl3 ; 75.5 MHz) δ24.3, 25.5, 28.8, 28.9, 29.7, 36.3, 38.8, 52.7, 104.0, 173.0; MS (70 eV) m/z (rel. intensity) 353 (1.90), 305 (9.00), 236 (8.14), 128 (6.94), 100 (8.59), 85 (20.70) 84 (40.52), 75 (100.00); HRMS (FAB) 433.3278 (MH+).

Quellen und Nachweise

ORD-Eintrag
ord-5cb410b6dcf04339819fcbbc5edc2948
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05336807

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