Ethyl chloroformate → Ethyl [3-(triethoxysilyl)propyl]carbamate

Participants

Reaction Conditions

Reaction Steps

3-Aminopropyltriethoxysilane (442 g.), light petroleum (b.p. 30°-40°, 1600 ml) and anhydrous triethylamine (255 g.) were placed under dry nitrogen in a three-necked flask equipped with a stirrer and dropping funnel. The mixture was cooled to -10° C. and a solution of redistilled ethyl chloroformate (217 g.) in light petroleum (b.p. 30°-40° C., 600 ml) was added dropwise over 2 h. The mixture was allowed to warm to ambient temperature and left overnight. The mixture was then rapidly filtered and the solid washed with light petroleum (2 × 300 ml). The combined filtrate was then concentrated and fractionally distilled to give ethyl-N-(3-triethoxysilylpropyl)carbamate (517 g.), b.p. 125°-135° C./0.09 mm.

Provenance & Evidence