2-Aminothiophenol → HCID 15027914, compound

Temperature

-5 °C

9.25 g (=0.07 m) of 2-aminothiophenol, 27.9 g of benzyltrimethylammonium chloride, and 25 g of sodium hydrogen carbonate were introduced into 150 ml of chloroform with stirring. The resulting suspension was cooled to -5° C., and a solution of 25.3 g of 2,6-dibromocaproic acid bromide in 70 ml of chloroform was added slowly with stirring to the cooled suspension. The addition took 30 minutes, and the temperature varied between -5° C. and +5° C. The mixture was maintained in this temperature range for a further hour. The mixture was then heated under reflux for 7 hours. Afterward it was cooled, filtered and the chloroform was distilled off from the filtrate. The remaining residue was treated with water and toluene. The organic phase was separated, dried, and fractionated by column chromatography. The fraction containing 2-(4-bromobutyl)-2H-1,4-benzothiazine-3(4H)-one was separated. After crystallization in the presence of diethyl ether, 5.9 g of 2 -(4-bromobutyl)-2H-1,4-benzothiazine-3(4H)-one were obtained from this fraction as slightly beige-colored crystals having a melting point of 100° C.

1. stirringwith stirring to the cooled suspension
2. additionThe addition
3. customvaried between -5° C. and +5° C
4. temperatureThe mixture was maintained in this temperature range for a further hour
5. temperatureThe mixture was then heated
6. temperatureunder reflux for 7 hours
7. temperatureAfterward it was cooled
8. filtrationfiltered
9. distillationthe chloroform was distilled off from the filtrate
10. additionThe remaining residue was treated with water and toluene
11. customThe organic phase was separated
12. customdried
13. additionThe fraction containing 2-(4-bromobutyl)-2H-1,4-benzothiazine-3(4H)-one
14. customwas separated
15. customAfter crystallization in the presence of diethyl ether

ORD record

ord-6afee48668d24280836745d15370d81c

Source dataset

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05283243