Chlorotrimethylsilane → HCID 69054736, compound

Temperature

60 °C

A suspension is prepared of 8 g (60 mM) of 2-(2-methylaminoethoxy)acetic acid in 100 ml of chloroform and 20 ml of acetonitrile, and, at ambient temperature, 17 ml (120 mM) of triethylamine are added, then, dropwise, 7.63 ml (60 mM) of chlorotrimethylsilane. The mixture is agitated at 60° C. for 2 hours and then cooled to ambient temperature and 17 ml (120 mM) of triethylamine and then 16.48 g (60 mM) of 4-methoxy-2-(trifluoromethyl)benzenesulphonyl chloride in solution in 60 ml of chloroform, are added slowly. The reaction mixture is kept under agitation at 5° C. for 16 hours, and then concentrated under reduced pressure. The residue is taken up into 150 ml of dichloromethane and is treated with 40 ml of an N solution of hydrochloric acid. The organic phase is separated, washed with water, and then extracted with twice 120 ml of N sodium hydroxide. The basic aqueous phase is separated, washed with 100 ml of dichloromethane and then acidified with a 5N solution of hydrochloric acid. The precipitate formed is extracted with twice 80 ml of dichloromethane; the organic phase obtained is washed with water and then dried over magnesium sulphate and concentrated under reduced pressure. The residue obtained is crystallised in isopropyl ether, separated off and dried. 6.32 g of the compound sought after are thus obtained as a white solid (yield=28%).

1. temperaturecooled to ambient temperature
2. waitThe reaction mixture is kept under agitation at 5° C. for 16 hours
3. concentrationconcentrated under reduced pressure
4. additionis treated with 40 ml of an N solution of hydrochloric acid
5. customThe organic phase is separated
6. washwashed with water
7. extractionextracted with twice 120 ml of N sodium hydroxide
8. customThe basic aqueous phase is separated
9. washwashed with 100 ml of dichloromethane
10. customThe precipitate formed
11. extractionis extracted with twice 80 ml of dichloromethane
12. customthe organic phase obtained
13. washis washed with water
14. dry with materialdried over magnesium sulphate
15. concentrationconcentrated under reduced pressure
16. customThe residue obtained
17. customis crystallised in isopropyl ether
18. customseparated off
19. customdried

ORD record

ord-080f8f58dcc245a5b19dfa7e88e883c8

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538111B2