Dimethylamine → HCID 10059268, compound

Temperature

15 °C

195 g of 3-trifluoromethylphenol are initially charged in 160 ml of 40% aqueous dimethylamine solution and cooled to 15° C. At 155° C., 108 ml of 37% aqueous formaldehyde solution are added dropwise within 40 min. Subsequently, the mixture is stirred at room temperature for 20 hours. The mixture is cooled again to 15° C., admixed with 8 ml of 40% aqueous dimethylamine solution and 5.5 ml of 37% aqueous formaldehyde solution are added dropwise. Subsequently, the mixture is stirred at room temperature for a further 4.5 hours. The mixture is cooled again to 15° C. and admixed with 32 ml of 40% aqueous dimethylamine solution, and 21 ml of 37% aqueous formaldehyde solution are added dropwise. Subsequently, stirring is continued at room temperature for 17 hours. The mixture is admixed with 150 ml of water. The organic phase is removed, the aqueous phase is extracted twice with dichloromethane, the combined organic phases are washed once with water and the solvent is distilled off under reduced pressure. The crude product is taken up in 250 ml of water and adjusted to pH 1-2 with cooling in an ice bath using dilute hydrochloric acid. The acidic solution is extracted once with dichloromethane and subsequently adjusted to pH 11 with cooling in an ice bath using dilute sodium hydroxide solution. The alkaline reaction solution is extracted twice with dichloromethane, the combined organic phases are washed once with water and dried, and the solvent is distilled off under reduced pressure. The crude product is subsequently fractionally distilled under reduced pressure. 186 g (71% of theory) of a light yellow liquid having a boiling point of 91° C. at 14 mbar are obtained.

1. temperatureThe mixture is cooled again to 15° C.
2. additionare added dropwise
3. stirringSubsequently, the mixture is stirred at room temperature for a further 4.5 hours
4. temperatureThe mixture is cooled again to 15° C.
5. additionare added dropwise
6. stirringSubsequently, stirring
7. waitis continued at room temperature for 17 hours
8. customThe organic phase is removed
9. extractionthe aqueous phase is extracted twice with dichloromethane
10. washthe combined organic phases are washed once with water
11. distillationthe solvent is distilled off under reduced pressure
12. temperaturewith cooling in an ice bath
13. extractionThe acidic solution is extracted once with dichloromethane
14. temperaturewith cooling in an ice bath
15. customThe alkaline reaction solution
16. extractionis extracted twice with dichloromethane
17. washthe combined organic phases are washed once with water
18. customdried
19. distillationthe solvent is distilled off under reduced pressure
20. distillationThe crude product is subsequently fractionally distilled under reduced pressure
21. customare obtained

ORD record

ord-90a14c34fe9046ca9be0ebe84d766441

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06903239B2