Triethylamine → HCID 12017139, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 0.5 g of oxalyl chloride in 15 mL of methylene chloride cooled to −78° C. was added 1 mL of anhydrous DMSO. After 15 min, a solution of 1 g of 3-[2-(3-hydroxy-propyl)-benzimidazol-1-yl]-propionitrile in 50 mL of methylene chloride and 10 mL of anhydrous DMSO was added while keeping the temperature below −50° C. There was considerable precipitate which redissolved on warming to 0° C. over 20 min. After cooling back down to −50° C., 5 mL of triethyl amine was added and the mixture allowed to warm to room temperature. After 15 min, the mixture was diluted with 250 mL of water, shaken and separated. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude 3-[2-(3-oxo-propyl)-Benzimidazol-1-yl]-propionitrile was an amber resin (1 g), and contained only traces of the starting alcohol by TLC (90:10 methylene chloride:methanol).

Provenance & Evidence