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Urea → 3-Cyclohexyl-5-ethoxy-1,3-dihydro-2H-benzimidazol-2-one

HRID 1081463
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HRID 1081463 반응식
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:5]=1)[CH3:2].N[C:19](N)=[O:20].CCOC(C)=O>CC1C=CC(C)=C(C)C=1C>[CH:12]1([N:11]2[C:6]3[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=[CH:8][C:7]=3[NH:10][C:19]2=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1176UreaHCID 8857Ethyl AcetateHCID 229225154-Ethoxy-1-amino-2-cyclohexylaminobenzene

생성물 1

HCID 152315443-Cyclohexyl-5-ethoxy-1,3-dihydro-2H-benzimidazol-2-one수율 39.3%

시약·촉매·용매 1

HCID 102631,2,3,4-Tetramethylbenzene용매

실험 절차

A mixture of 3.05 g of the oil obtained in step B) and 1.6 g of urea in 8 ml of 1,2,3,4-tetramethylbenzene is heated at 170°-180° C. for 1 hour 30 minutes. After cooling, it is taken up with AcOEt, washed with water and dried over sodium sulfate and the solvent is evaporated off under vacuum. The residue is taken up with hexane and the brown precipitate formed is filtered off. The precipitate is chromatographed on silica using a DCM/AcOEt mixture (50/50; v/v) as the eluent to give 1.33 g of the expected product, which was precipitated with isopropyl ether. M.p.=203° C.

후처리

  1. temperatureis heated at 170°-180° C. for 1 hour 30 minutes
  2. temperatureAfter cooling
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated off under vacuum
  6. customthe brown precipitate formed
  7. filtrationis filtered off
  8. customThe precipitate is chromatographed on silica using a DCM/AcOEt mixture (50/50; v/v) as the eluent

출처 및 근거

ORD 기록
ord-31f58be9b0f541ac87ac226a98d031d2
출처 데이터셋
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05585394

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