Chlorotrimethylsilane → N,N'-bis-trimethylsilyl-N,N'-methylene-bis-acrylamide

HRID 2419190Notes

Reaction equation

[CH2:1]([NH:7][C:8](=[O:11])[CH:9]=[CH2:10])[NH:2][C:3](=[O:6])[CH:4]=[CH2:5].[CH3:12][Si:13]([CH3:16])([CH3:15])Cl.[S]>C(N(CC)CC)C>[CH3:12][Si:13]([CH3:16])([CH3:15])[N:7]([CH2:1][N:2]([Si:13]([CH3:16])([CH3:15])[CH3:12])[C:3](=[O:6])[CH:4]=[CH2:5])[C:8](=[O:11])[CH:9]=[CH2:10]

Participants

Conditions

Temperature: 60 °C

Procedure

850 ml of anhydrous triethylamine and 92.5 g (0.6 mol) of N,N'-methylene-bis-acrylamide are initially introduced into a 2.5 liter sulphonation flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel. 220 g (approximately 2 mols) of trimethylchlorosilane are then added dropwise, whilst cooling occasionally with an ice bath, in such a way that the temperature of the reaction mixture does not exceed 15°-25° C. A little sulphur is then added, as a polymerisation inhibitor, to the reaction mixture, which is stirred overnight at 60° C. The following day, the triethylamine hydrochloride which has precipitated is filtered off, the filter cake is washed with approximately 300 ml of triethylamine, and the filtrates are finally combined and distilled in vacuo. 108 g of N,N'-bis-trimethylsilyl-N,N'-methylene-bis-acrylamide are obtained as a fraction distilling at 120° C/0.8 mm Hg.

Workup

customequipped with a stirrer
temperaturewhilst cooling occasionally with an ice bath
customdoes not exceed 15°-25° C
customThe following day, the triethylamine hydrochloride which has precipitated
filtrationis filtered off
washthe filter cake is washed with approximately 300 ml of triethylamine
distillationdistilled in vacuo

Sources & evidence

ORD record: ord-42f85e4ec27247d683166b9eca06d641
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04105648

Reaction notes

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