Dimethyl Sulfoxide → HCID 54237436, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of DMSO (7.58 g, 97.0 mmol) in CH2Cl2 (100 μL) at −78° C. was added oxalyl chloride (6.16 g, 48.5 mmol) over the course of 10 min. After an additional 15 min at −78° C., a solution of 3-chloro-5-N,N-dimethylaminobenzyl alcohol (8.18 g, 44.1 mmol; see step (i) above) in CH2Cl2 (100 mL) was added over the course of 15 min. The resulting solution was stirred at −78° C. for 1 h prior to the addition of DIPEA (28.5 g, 220.5 mmol). The solution was warmed to 25° C. and stirred for 18 h, before being concentrated in vacuo to give the crude product. Flash chromatography on silica gel, eluting with Hex:EtOAc (5:1), gave 7.50 g (93%) of the sub-title compound as a yellow solid.

Provenance & Evidence