Diethylcarbamoyl chloride → HCID 66771878, compound

Participants

Reaction Conditions

Reaction Steps

Charge a vessel with 2-(4-methoxy-phenyl)-benzo[b]thiophen-6-ol (1.000 mol, 256.3 g), 99% DMAP (0.100 mol, 12.34 g), and THF (10.0 L/kg, 2.56 L). Add 99% triethylamine (1.050 mol, 107.3 g) and 97% diethylcarbamyl chloride (DEC-Cl) (1.050 mol, 146.8 g). Heat the contents of the reactor to reflux/66° C. Stir 4 hours or until reaction is complete as determined by HPLC. Begin to cool to 50° C. and add acetic acid solution made up of DI water (3.0 L/kg, 769 mL) and glacial acetic acid (0.300 mol, 18.02 g). Separate the layers at 50° C., and remove the bottom aqueous layer. Cool the organic layer to −5 to 0° C. (−20° C. to ambient is acceptable). The organic layer contains a solution of diethyl-carbamic acid 2-(4-methoxy-phenyl)-benzo[b]thiophen-6-yl ester which is most conveniently carried directly to the next step, the bromination step.

Provenance & Evidence