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m-Chloroperbenzoic acid → 6-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole

HRID 1847994
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HRID 1847994 반응식
[Br:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][C:8]2[CH:18]=[CH:17][C:11]3[N:12]=[C:13]([S:15][CH3:16])[S:14][C:10]=3[CH:9]=2)[CH:6]=1.ClC1C=C(C=CC=1)C(OO)=[O:24].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][C:8]2[CH:18]=[CH:17][C:11]3[N:12]=[C:13]([S:15]([CH3:16])=[O:24])[S:14][C:10]=3[CH:9]=2)[CH:6]=1
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참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 866810186-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole

생성물 1

HCID 866810196-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole수율 121.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a stirred mixture of 6-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole (105 mg, 0.3 mmol) from Step 5 of this Example in CH2Cl2 (15 mL) at 0° C. was added 70-75% 3-chloroperoxybenzoic acid (91 mg, 0.4 mmol). After the mixture was stirred at 0° C. for 2 h, saturated aq NaHCO3 (10 mL) was added. The mixture was stirred for 10 min and the CH2Cl2 layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 6-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole (130 mg) as a white foam. The material was used in the next step without further purification. LCMS (ESI) m/z 356 and 358 (M+H)+.

후처리

  1. customat 0° C.
  2. stirringThe mixture was stirred for 10 min
  3. customthe CH2Cl2 layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9a3746ebd365426e80a1578374fe26e3
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952058B2

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