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

Temperature

0 °C

To the 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 minutes at 0° C. The reaction solution was stirred at 0° C. for 20 min and then at RT. for 2 hr. The reaction mixture was concentrated to a solid. To the residual solids add 200 ml of ethyl acetate and 50 ml of water and stir at RT. for 10 minutes. With stirring, carefully add excess solid NaHCO3 until basic. Stir at RT. about 1 hour to dissolve the solids. Remove the aqueous layer and extract with 100 ml of ethyl acetate. Combine organic layers and wash with 1×30 ml water, 1×25 ml saturated NaCl solution and dry with sodium sulfate. This mixture was filter through a silica gel plug (1.25 in.×3 in.) and flushed with ethyl acetate. The filtrate was concentrated under reduced pressure to give 2-(cyclohexylmethylamino)benzo[d]thiazol-6-ol as solid (1.32 grams). ES/MS m/z 263.1 (MH+).

1. customat RT
2. waitfor 2 hr
3. concentrationThe reaction mixture was concentrated to a solid
4. additionTo the residual solids add 200 ml of ethyl acetate and 50 ml of water
5. stirringstir at RT
6. waitfor 10 minutes
7. stirringWith stirring
8. stirringStir at RT
9. dissolutionabout 1 hour to dissolve the solids
10. customRemove the aqueous layer
11. extractionextract with 100 ml of ethyl acetate
12. washCombine organic layers and wash with 1×30 ml water, 1×25 ml saturated NaCl solution
13. dry with materialdry with sodium sulfate
14. filtrationThis mixture was filter through a silica gel plug (1.25 in.×3 in.)
15. customflushed with ethyl acetate
16. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-41f8324902224080b52647cdf5ae0e3f

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710048B2