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1,1'-Carbonyldiimidazole → 5-Bromo-6-(2,4-difluorophenoxy)-1,3-dihydro-2H-benzimidazol-2-one

HRID 629295
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HRID 629295 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([NH2:17])=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16].C1N=CN([C:24](N2C=NC=C2)=[O:25])C=1>C(OCC)(=O)C>[Br:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[CH:6][C:5]2[NH:17][C:24](=[O:25])[NH:18][C:4]=2[CH:3]=1
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참가 물질

4

반응물 2

HCID 682631,1'-Carbonyldiimidazole2회HCID 1180936764-Bromo-5-(2,4-difluorophenoxy)benzene-1,2-diamine

생성물 1

HCID 1180936705-Bromo-6-(2,4-difluorophenoxy)-1,3-dihydro-2H-benzimidazol-2-one수율 39%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

A solution of 4-bromo-5-(2,4-difluorophenoxy)benzene-1,2-diamine (0.371 g, 1.18 mmol) in ethyl acetate (5.20 mL) was treated with N,N-carbonyldiimidazole (0.23 g, 1.4 mmol) and stirred at 50° C. for 30 min. The reaction mixture was treated with additional N,N-carbonyldiimidazole (1.2 eq) and stirred at 50° C. for 1 h. The reaction mixture was cooled to 20° C. and the heterogeneous mixture was filtered to give the desired product (156 mg, 39%) as a light grey solid. LCMS calculated for C13H8BrF2N2O2 (M+H)+: m/z=341.0, 343.0. found: 341.0, 342.9.

후처리

  1. stirringstirred at 50° C. for 1 h
  2. temperatureThe reaction mixture was cooled to 20° C.
  3. filtrationthe heterogeneous mixture was filtered

출처 및 근거

ORD 기록
ord-c1d26d6cfcb74444942ccb70b51f5a20
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09315501B2

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