Thionyl Chloride → HCID 68295574, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2,4-dimethylbenzoyl)benzoic acid (50 g, 197 mmol) and thionyl chloride (215 mL, 2949 mmol) was heated at 70° C. for 1.5 hours. The mixture was concentrated, dissolved in tetrahydrofuran (THF) (200 mL) and N,N-dimethylformamide (DMF) (40 mL) and treated with methyl N-methylglycinate (27.4 g, 197 mmol). The mixture was cooled to 0° C. and treated with Hunig's base (103 mL, 590 mmol). The mixture was heated to 70° C. for 1 hour, cooled to ambient temperature and then diluted with ethyl acetate. The organic phase was washed with 1N HCl, water, then brine, dried over sodium sulfate, filtered and concentrated to a brown thick oil (60 g, 90%) which was used without further purification. LC/MS (m/z) ES+=340 (M+1).

Provenance & Evidence