N-Benzylideneaniline → 1-Propanamine, N-(phenylmethylene)-3-(trimethoxysilyl)-

HRID 890848Notes

Reaction equation

[CH:1](=[N:8][C:9]1C=CC=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NCCC[Si:19]([O:24][CH3:25])([O:22][CH3:23])[O:20][CH3:21].[SiH4]>C1(C)C(C)=CC=CC=1>[C:2]1([CH:1]=[N:8][CH2:9][CH2:10][CH2:11][Si:19]([O:24][CH3:25])([O:22][CH3:23])[O:20][CH3:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

25 grams (0.138 moles) of N-benzylidene aniline [cas no. 538-51-2, from TCI America] was combined with 24.7 grams (0.138 moles) of gamma-aminopropyltrimethoxysilane [cas no. 13822-56-5, Silquest A-1110 Silane from Crompton Corporation] and 100 grams of xylene. The resulting slurry was warmed to 90° C. for one hour before a vacuum of 20 mm Hg was applied. Distillation of the xylene and aniline resulted in 36 grams (98%) of N-benzylidene aminopropyltrimethoxysilane [cas no. 67674-55-9] by GC analysis.

Workup

distillationDistillation of the xylene and aniline
customresulted in 36 grams (98%) of N-benzylidene aminopropyltrimethoxysilane [cas no

Sources & evidence

ORD record: ord-f36fbff332df47769964876f6c3f4a53
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06998499B2

Reaction notes

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