N,N-Dimethyl-1,3-propanediamine → N-(3-Dimethylaminopropyl)-N'-(3-Triethoxysilylpropyl)Urea

HRID 236633

Reaction equation

HRID 236633 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][Si:7]([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[C:2]=[O:3].[CH3:17][N:18]([CH3:23])[CH2:19][CH2:20][CH2:21][NH2:22]>>[CH3:17][N:18]([CH3:23])[CH2:19][CH2:20][CH2:21][NH:22][C:2]([NH:1][CH2:4][CH2:5][CH2:6][Si:7]([O:14][CH2:15][CH3:16])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])=[O:3]

Participants

3

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 90613Triethoxy(3-isocyanatopropyl)silane

Product 1

HCID 20216491N-(3-Dimethylaminopropyl)-N'-(3-Triethoxysilylpropyl)Urea

Procedure

To a stirred solution of 3-isocyanatopropyltriethoxysilane (74 g; 0.31 mole) was slowly added 30 g (0.30 mole) of N,N-dimethyl-1,3-propanediamine. There was a significant exotherm. The product was purified by strip distillation at 205° C. (0.1 torr). NMR (CDCl3) 0.40-0.9 (m; 2H), 1.22 (t; 9H), 1.4-1.9 (m; 4H), 2.21 (s; 6H), 2.33 (t; 2H), 2.9-3.4 (m; 4H), 3.81 (q; 6H), 5.8 (b, 2H) ppm. IR (neat film) 3340, 2980, 2940, 1635, 1575, 1105, 1080, 960, 780 cm-1.

Workup

  1. distillationThe product was purified by strip distillation at 205° C. (0.1 torr)

Sources & evidence

ORD record
ord-4a68e44d4c944bd38f3565ecfbc2d504
Source dataset
uspto-grants-1987_02
Patent number
US04645846

Linked notes

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