Boron tribromide → 2-(Cyclohexylmethylamino)benzo[d]thiazol-6-ol

온도

0 °C

To a solution of N-(cyclohexylmethyl)-6-methoxybenzo[d]thiazol-2-amine (1.40 g, 5.05 mmol) in 12 mL of DCM was added 1 M boron tribromide in DCM (10.6 mL, 10.6 mmol) slowly over about 3 min at 0° C. The reaction solution was stirred at 0° C. for 20 min and at room temperature for additional 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and water (50 mL) and the mixture was stirred at room temperature for 10 min. To the mixture was carefully added excess of solid NaHCO3 until basic and stirring was continued for 1 hour. The mixture was phase separated and the aqueous layer was extracted with EtOAc (100 mL). The combined organic layers were washed with water (30 mL), saturated NaCl solution (25 mL) and dried over sodium sulfate. This mixture was filter through a plug of silica gel and concentrated under reduced pressure to give the title compound as a solid (1.32 grams). ES/MS m/z 263.1 (MH+).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionThe residue was dissolved in EtOAc (200 mL)
3. stirringwater (50 mL) and the mixture was stirred at room temperature for 10 min
4. stirringstirring
5. waitwas continued for 1 hour
6. customseparated
7. extractionthe aqueous layer was extracted with EtOAc (100 mL)
8. washThe combined organic layers were washed with water (30 mL), saturated NaCl solution (25 mL)
9. dry with materialdried over sodium sulfate
10. filtrationThis mixture was filter through a plug of silica gel
11. concentrationconcentrated under reduced pressure

ORD 기록

ord-916d334978c0454ab6ee1a0171e138c7

출처 데이터셋

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08293769B2