Dimethylformamide → HCID 22478019, compound

A magnetically stirred mixture of acid 4-chloro-2-methylbenzoic acid (50 g, 0.29 mol), dichloromethane (200 mL), and 0.5 mL DMF was cooled in an ice-bath. The cooler was connected to a gas absorption trap. Oxalyl chloride (44.5 g, 0.35 mmol) was added dropwise in 1 h. The mixture was stirred at r.t. overnight during which time all solid dissolved. The solution was concentrated in vacuo and stripped with dichloromethane to remove excess oxalyl chloride. The residue was taken in THF (200 mL) and mechanically stirred in an ice-water bath. Aqueous 25% ammonia (100 mL) was added in 15 min, which resulted in the formation of a precipitate. The THF was removed with the rotavap and extra water (100 mL) was added. The suspension was stirred at r.t. overnight. The solid was collected by filtration and dried in vacuo to give 2-methyl-4-chlorobenzamide (43.7 g, yield 89%) that was used without purification in the next step.

1. temperaturewas cooled in an ice-bath
2. customThe cooler was connected to a gas absorption trap
3. dissolutiondissolved
4. concentrationThe solution was concentrated in vacuo
5. customto remove excess oxalyl chloride
6. stirringmechanically stirred in an ice-water bath
7. additionAqueous 25% ammonia (100 mL) was added in 15 min
8. customwhich resulted in the formation of a precipitate
9. customThe THF was removed with the rotavap and extra water (100 mL)
10. additionwas added
11. stirringThe suspension was stirred at r.t. overnight
12. filtrationThe solid was collected by filtration
13. customdried in vacuo

ORD record

ord-b35d51d6868f41dcbfa20a9f49cbd5f2

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09420788B2