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

HRID 1081463
ノート
印刷プレビュー

反応式

HRID 1081463 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 102631,2,3,4-Tetramethylbenzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-31f58be9b0f541ac87ac226a98d031d2
出典データセット
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05585394

反応ノート

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