Triethylamine → HCID 22251058, compound

Temperature

25 °C

A mixture of 5-chloro-o-anisic acid (50 g, 0.27 mol), oxalyl chloride (23 mL, 0.27 mol) and methylene chloride was stirred 1 hour at approximately 25° C. and then treated with DMF (2 drops). The mixture was stirred an additional hour, heated 45 minutes at reflux and then concentrated. The residue was dissolved in THF and the solution was reconcentrated. The residue was dissolved in THF-(approximately 200 mL) and the solution was added in a thin stream to a mixture of triethylamine (96 mL, 0.7 mol), N,O-dimethylhydroxylamine hydrochloride (26.3 g, 0.27 mol) and methylene chloride (approximately 300 mL). After an exothermic reaction had ensued, the mixture was allowed to cool to 25° C. and stirred approximately 16 hours. The mixture was filtered, concentrated and then partitioned between ethyl acetate and water. The organic layer was separated, washed with water (2×), sodium bicarbonate. (2×), 2% hydrochloric acid (1×) and brine (1×), dried (K2CO3), filtered and concentrated to give N-methoxy-N-methyl-5-chloro-2-methoxy-benzamide (52.3 g, 0.23 mmol), m.p. 80°-83° C.

1. stirringThe mixture was stirred an additional hour
2. temperatureheated 45 minutes
3. temperatureat reflux
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in THF
6. dissolutionThe residue was dissolved in THF-(approximately 200 mL)
7. customAfter an exothermic reaction
8. temperatureto cool to 25° C.
9. stirringstirred approximately 16 hours
10. filtrationThe mixture was filtered
11. concentrationconcentrated
12. custompartitioned between ethyl acetate and water
13. customThe organic layer was separated
14. washwashed with water (2×), sodium bicarbonate
15. dry with material(2×), 2% hydrochloric acid (1×) and brine (1×), dried (K2CO3)
16. filtrationfiltered
17. concentrationconcentrated

ORD record

ord-05e8a828f92a43acb655bb065083bf35

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05739336