Reaktion #2075640

Reaktionsgleichung

N-(cyclohexylmethyl)-6-methoxybenzo[d]thiazol-2-amine

boron tribromide

→

2-(cyclohexylmethylamino)benzo[d]thiazol-6-ol

Ausbeute 99.6%

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat RT
2. 2
   workup.WAITfor 2 hr
3. 3
   EinengenThe reaction mixture was concentrated to a solid
4. 4
   workup.ADDITIONTo the residual solids add 200 ml of ethyl acetate and 50 ml of water
5. 5
   workup.STIRRINGstir at RT
6. 6
   workup.WAITfor 10 minutes
7. 7
   workup.STIRRINGWith stirring
8. 8
   workup.STIRRINGStir at RT
9. 9
   workup.DISSOLUTIONabout 1 hour to dissolve the solids
10. 10
    SonstigeRemove the aqueous layer
11. 11
    Extraktionextract with 100 ml of ethyl acetate
12. 12
    WaschenCombine organic layers and wash with 1×30 ml water, 1×25 ml saturated NaCl solution
13. 13
    Trocknendry with sodium sulfate
14. 14
    FiltrationThis mixture was filter through a silica gel plug (1.25 in.×3 in.)
15. 15
    Sonstigeflushed with ethyl acetate
16. 16
    EinengenThe filtrate was concentrated under reduced pressure

Vorschrift

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+).

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