Chlorotrimethylsilane → HCID 131711178, compound

HRID 2419189Notes

Reaction equation

[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].[CH3:6][Si:7]([CH3:10])([CH3:9])Cl>C(N(CC)CC)C>[CH3:6][Si:7]([C:3]([Si:7]([CH3:10])([CH3:9])[CH3:6])=[CH:2][C:1]([NH2:5])=[O:4])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

71 g (1 mol) of acrylic acid amide are dissolved in 750 ml of anhydrous triethylamine in a 6 liter three-necked flask equipped with a stirrer and a reflux condenser. 270 g (2.5 mols) of trimethylchlorosilane are then added dropwise over the course of 2 hours at room temperature (approximately 25° C). The temperature is then slowly raised to 60° C and the reaction mixture is stirred for about 16 hours at this temperature. The triethylamine hydrochloride which has precipitated is filtered off under protective gas and the filter cake obtained is rinsed with 200 ml of triethylamine. The triethylamine is then distilled off under a slight vacuum at 40°-45° C. The resulting concentrated filtrate is subjected to a purification distillation with addition of a little sulphur as a polymerisation inhibitor. 149 g (69% of theory) of bis-trimethylsilylacrylic acid amide, boiling at 71° C/20 mm Hg, are obtained.

Workup

customequipped with a stirrer and a reflux condenser
customThe triethylamine hydrochloride which has precipitated
filtrationis filtered off under protective gas
customthe filter cake obtained
washis rinsed with 200 ml of triethylamine
distillationThe triethylamine is then distilled off under a slight vacuum at 40°-45° C
distillationThe resulting concentrated filtrate is subjected to a purification distillation with addition of a little sulphur as a polymerisation inhibitor

Sources & evidence

ORD record: ord-f18e48bfcac24901bb77bde7705e7fbe
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04105648

Reaction notes

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