Bromine → 2-Amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one

5,5-Dimethyl-cyclohexane-1,3-dione (201 g, 1.43 mol) and NaOAc (176 g, 2.14 mol) are suspended in AcOH (2 L) and Br2 (229 g, 1.43 mol) is added in dropwise while maintaining the reaction temperature between 15 and 20° C. After complete addition, the reaction is stirred at RT overnight. Thiourea (109 g, 1.43 mol) is added in portions and the reaction mixture is heated at 100° C. for 1 h. After cooling to RT, the AcOH is removed in vacuo and the resulting crude product is diluted with water (1 L) and neutralized with an aqueous saturated NaHCO3 solution. The resulting mixture is extracted with ethyl acetate (4×500 mL). The organic layer is washed with brine (500 mL), dried over anhydrous Na2SO4 and the solvent is evaporated in vacuo to give crude product. The crude product is washed with water (1.5 L) to yield 2-amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one (211 g, 75% yield).

1. temperaturewhile maintaining the reaction temperature between 15 and 20° C
2. additionAfter complete addition
3. temperaturethe reaction mixture is heated at 100° C. for 1 h
4. temperatureAfter cooling to RT
5. customthe AcOH is removed in vacuo
6. additionthe resulting crude product is diluted with water (1 L)
7. extractionThe resulting mixture is extracted with ethyl acetate (4×500 mL)
8. washThe organic layer is washed with brine (500 mL)
9. dry with materialdried over anhydrous Na2SO4
10. customthe solvent is evaporated in vacuo
11. customto give crude product
12. washThe crude product is washed with water (1.5 L)

ORD-Eintrag

ord-d4cdbd65aaa3462697dbdaa6824b1482

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09243000B2