Bromine → 6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine

HRID 538866노트

반응식

HRID 538866 반응식
[CH3:1][N:2]([CH3:19])[CH:3]([CH2:17][CH3:18])[CH:4]([C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[C:20]([S-:22])#[N:21].[K+].BrBr>CC(O)=O>[CH3:1][N:2]([CH3:19])[CH:3]([CH2:17][CH3:18])[CH:4]([C:10]1[CH:16]=[CH:15][C:13]2[N:14]=[C:20]([NH2:21])[S:22][C:12]=2[CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1

참가 물질

5

반응물 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 866818954-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)aniline

생성물 1

HCID 547593306-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

Step-7: A solution of 4-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)aniline (600 mg, 2.32 mmol) and KSCN (508 mg, 5.22 mmol) in 15 mL AcOH was cooled to about 7° C. and treated with Br2 (125 μL, 2.43 mmol) in 2 mL AcOH added drop-wise via syringe over 5 min. The reaction vessel was removed from the cooling bath and stirred at rt for 1 hr. The reaction was cooled in an ice bath and basified with 3N NaOH (100 mL) added portionwise over several minutes. This mixture was then extracted with DCM (4×75 mL). The combined organic extracts were dried over Na2SO4, decanted and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 6% MeOH (2N NH3)/DCM to give 6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine as a yellow foam. MS ESI: m/z 316.16 [M+1+].

후처리

  1. customThe reaction vessel was removed from the cooling bath
  2. temperatureThe reaction was cooled in an ice bath
  3. additionadded portionwise over several minutes
  4. extractionThis mixture was then extracted with DCM (4×75 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. customdecanted
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with 6% MeOH (2N NH3)/DCM

출처 및 근거

ORD 기록
ord-8ffccf12dbda434784c72b36f7b57182
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865752B2

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