Thionyl Chloride → HCID 403394, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-[(2-hydroxy-1,1-dimethylethyl)carbamoyl]benzoate (100 mg, 0.40 mmol) in CDCl3 (2 mL) was added thionyl chloride (57 mg, 0.48 mmol). The mixture was heated to 60° C. in a sealed tube for 4 h. After cooling, the reaction was quenched by pouring onto saturated aqueous NaHCO3 (20 mL). After extraction with dichloromethane (3×20 mL), the combined organic extracts were washed with brine (20 mL), dried (MgSO4), filtered and concentrated at reduced pressure. Purification by silica FCC (eluting with 20:80 heptane/EtOAc) gave the title compound (78 mg, 84% yield) as colourless oil.

Provenance & Evidence