Hydrogen Bromide → 1-(2-bromobenzo[d]thiazol-6-yl)-1-(1H-imidazol-1-yl)-N,N-dimethylbutan-2-amine

HRID 1894754Notes

Reaction equation

HRID 1894754 reaction equation
[CH3:1][N:2]([CH3:22])[CH:3]([CH2:20][CH3:21])[CH:4]([C:10]1[CH:19]=[CH:18][C:13]2[N:14]=[C:15](N)[S:16][C:12]=2[CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[BrH:23].N([O-])=O.[Na+]>O>[Br:23][C:15]1[S:16][C:12]2[CH:11]=[C:10]([CH:4]([N:5]3[CH:9]=[CH:8][N:7]=[CH:6]3)[CH:3]([N:2]([CH3:22])[CH3:1])[CH2:20][CH3:21])[CH:19]=[CH:18][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 23668193Sodium NitriteHCID 547593306-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine

Product 1

HCID 547620851-(2-bromobenzo[d]thiazol-6-yl)-1-(1H-imidazol-1-yl)-N,N-dimethylbutan-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
-10 °C

Procedure

To a mixture of 6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine (4.75 g, 15.06 mmol) and water (46 mL) at 0° C. was added aqueous HBr (18.5 mL) and the mixture was cooled to −10° C. A cold (−10° C.) solution of sodium nitrite (1.3 g) in water (15 mL) was added to the reaction mixture over a period of 10 min while maintaining the temperature below −5° C. and the reaction was stirred at −10° C. for 15 min. To the reaction mixture was added a cold (−10° C.) solution of CuBr2 in water (46 mL), cooling bath was removed and stirred for 3 h. The reaction was basified using aqueous sodium carbonate, filtered through a pad of celite and extracted with DCM. The DCM extract was washed with water, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography using 0 to 2% methanol in DCM as eluent to afford 1-(2-bromobenzo[d]thiazol-6-yl)-1-(1H-imidazol-1-yl)-N,N-dimethylbutan-2-amine. MS ESI: m/z 400.9 [M+Na+].

Workup

  1. temperaturewhile maintaining the temperature below −5° C.
  2. temperaturecooling bath
  3. customwas removed
  4. stirringstirred for 3 h
  5. filtrationfiltered through a pad of celite
  6. extractionextracted with DCM
  7. extractionThe DCM extract
  8. washwas washed with water
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-248601663aa54bb1a906180c8aabc0de
Source dataset
uspto-grants-2013_08
Patent number
US08513291B2

Reaction notes

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