Triethylamine → (S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide

Temperature

-78 °C

To a solution of oxalyl chloride (4.5 ml) in dichloromethane (100 mL) at −78° C., dimethylsulfoxide (7.4 mL) in dichlororomethane (40 mL) was added. After the addition was complete, the solution was stirred for another 30 minutes at −78° C. A solution of (S)—N-[2-(3,4-dichloro-phenyl)-4-hydroxy-butyl]-N-methyl-benzamide (14.6 g) in dichloromethane (35 mL) and dimethylsulfoxide (7 ml) was then added drop wise. The solution was stirred at −78° C. for one hour. Triethylamine (29 mL) was added drop wise to the reaction and after 20 minutes the ice bath was removed and the solution was stirred at ambient temperature for 30 minutes. The reaction mixture was diluted with dichloromethane (200 mL), and washed with dilute aqueous hydrochloric acid (150 mL), water (150 mL), and aqueous sodium bicarbonate (150 mL). The separated organic layer was dried and evaporated then dissolved in ether. The white precipitate that formed, was filtered and dried giving the title compound (9.1 g). Rf=0.41 methylene chloride:methanol (95:5).

1. additionAfter the addition
2. stirringThe solution was stirred at −78° C. for one hour
3. customwise to the reaction
4. customafter 20 minutes the ice bath was removed
5. stirringthe solution was stirred at ambient temperature for 30 minutes
6. additionThe reaction mixture was diluted with dichloromethane (200 mL)
7. washwashed with dilute aqueous hydrochloric acid (150 mL), water (150 mL), and aqueous sodium bicarbonate (150 mL)
8. customThe separated organic layer was dried
9. customevaporated
10. dissolutionthen dissolved in ether
11. customThe white precipitate that formed
12. filtrationwas filtered
13. customdried

ORD record

ord-39185eed3e0e48dd80c14dc8b8d552b3

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07368461B2