Dimethylformamide → N-methoxy-N-methyl-3-(methylthio)benzamide

To a stirred solution of 3-(methylthio)benzoic acid (15.4 g, 91.5 mmol), cooled to 0° C. with a brine/ice bath, was added N,N-dimethylformamide (0.35 mL, 4.6 mmol) followed by oxalyl chloride (8.79 mL, 100 mmol). The resulting mixture was stirred 2 h at room temperature, until gas evolution stopped and a clear solution was obtained. The mixture was cooled to 0° C. with a brine/ice bath, N,O-Dimethylhydroxylamine (10.7 g, 110 mmol) was added at once, followed by dropwise addition of triethylamine (43.4 mL, 311 mmol) through a dropping funnel, while keeping the internal temperature under 20° C. The resulting suspension was stirred overnight at room temperature, filtered over a pad of silica gel, and concentrated in vacuo to afford N-methoxy-N-methyl-3-(methylsulfanyl)benzamide as an oil [19.9 g, yield 83%; HPLC/MS: m/z=212 (M+H); logP(HCOOH)=1.89].

1. customa clear solution was obtained
2. temperatureThe mixture was cooled to 0° C. with a brine/ice bath
3. customunder 20° C
4. stirringThe resulting suspension was stirred overnight at room temperature
5. filtrationfiltered over a pad of silica gel
6. concentrationconcentrated in vacuo

ORD record

ord-e1da17b5e04d4511a8753c74d18a57a2

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466176B2