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

HRID 538870노트

반응식

HRID 538870 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매3회

반응 조건

온도
-10 °C

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-4c19a76cb2004d058ce2c97810fa0255
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865752B2

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