Water → N,4-Dimethoxy-N-methylbenzamide

Temperature

2.5 °C

14.7 g (151 mmol) of N,O-dimethylhydroxylamine hydrochloride are added portionwise to a solution of 25 g (147 mmol) of 4-methoxybenzoyl chloride in 450 mL of dichloromethane, stirred at 0-5° C. under nitrogen. 51 mL (370 mmol) of triethylamine are then added slowly to the mixture stirred at 0-5° C. The orange-coloured reaction medium is stirred at room temperature for 3 hours. The mixture is hydrolysed with 250 mL of water and then extracted with dichloromethane. The organic phase is washed with 100 mL of 1N HCl, 150 mL of 1N NaOH and then with water and brine. It is dried over anhydrous sodium sulfate, filtered and evaporated to dryness. 26.9 g of an orange-coloured oil are obtained, and are purified on a column of silica, eluting with dichloromethane and then with a 95/5 dichloromethane/methanol mixture. 25.4 g of a yellow oil are obtained (89% yield).

1. stirringstirred at 0-5° C
2. stirringThe orange-coloured reaction medium is stirred at room temperature for 3 hours
3. extractionextracted with dichloromethane
4. washThe organic phase is washed with 100 mL of 1N HCl, 150 mL of 1N NaOH
5. dry with materialIt is dried over anhydrous sodium sulfate
6. filtrationfiltered
7. customevaporated to dryness

ORD record

ord-1a7a4476853546789fd83ac4eb4367e7

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07423030B2