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1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(4'-bromo-[1,1'-biphenyl]-2-yl)propane-2-sulfonamide

HRID 746763
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인쇄 미리보기

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HRID 746763 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.[CH:26]([S:29](Cl)(=[O:31])=[O:30])([CH3:28])[CH3:27]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][S:29]([CH:26]([CH3:28])[CH3:27])(=[O:31])=[O:30])=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2회HCID 824082-Propanesulfonyl chloride2회HCID 113686332-(4'-Bromophenyl)aniline

생성물 1

HCID 57974945N-(4'-bromo-[1,1'-biphenyl]-2-yl)propane-2-sulfonamide수율 75.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Add 4′-bromo-biphenyl-2-ylamine (1.038 g, 4.183 mmol) to CH2Cl2 and cool to 0° C. Add first DBU (2.6 ml, 17.038 mmol), then isopropylsulfonyl chloride (0.95 ml, 8.206 mmol) drop wise to flask and warm flask to room temperature. After 18 hours monitor reaction. If SM is still present, add DBU (1 ml), then isopropylsulfonyl chloride (0.4 ml) and then stir 2 additional hours. Purify resultant product using flash chromatography (Silica gel-25% EtOAc/Hexane) to provide propane-2-sulfonic acid (4′-bromo-biphenyl-2-yl)-amide (1.116 g, 75%). MS(m/e): 351.9(M−1).

후처리

  1. customreaction
  2. customPurify resultant product

출처 및 근거

ORD 기록
ord-4d3690aded9b44a298c16f635dbc3d8a
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07393868B2

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