Salicylic Acid → 2-Hydroxy-N,N-dimethylbenzamide

A mixture of 156 g (1.13 mol) of salicylic acid and 471 g (3.96 mol) of thionyl chloride was stirred for 4 hr at 50° C.-60° C. Excess thionyl chloride was distilled off under vacuum, and the residue was additionally dried in vacuum. A solution of this product in 300 mL of dichloromethane was added dropwise with vigorous stirring to a mixture of 270 g (3.31 mol) of dimethylamine hydrochloride and 702 g (6.95 mol) of triethylamine in 1200 mL of dichloromethane for 1 hr at 0° C. The resulting mixture was slowly warmed to room temperature, stirred for 1 hr, and then filtered through glass frit. The precipitate was additionally washed with 300 mL of dichloromethane. The combined filtrate was washed by 5% hydrochloric acid, water, dried over K2CO3, and then evaporated to dryness. The residue was washed with 200 mL of diethyl ether to yield 112 g (60%) of white solid.

1. distillationExcess thionyl chloride was distilled off under vacuum
2. customthe residue was additionally dried in vacuum
3. additionA solution of this product in 300 mL of dichloromethane was added dropwise
4. stirringstirred for 1 hr
5. filtrationfiltered through glass frit
6. washThe precipitate was additionally washed with 300 mL of dichloromethane
7. washThe combined filtrate was washed by 5% hydrochloric acid, water
8. dry with materialdried over K2CO3
9. customevaporated to dryness
10. washThe residue was washed with 200 mL of diethyl ether

ORD record

ord-b57cc6c6e1cc41838e205ce1ec2a0e21

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546501B2