Cyanamide → 2-[4-(2-amino-5-methyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethanol

HRID 967810

반응식

HRID 967810 반응식
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]([CH3:20])[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)=[CH:6][CH:5]=1.[N:21]#[C:22][NH2:23]>C(O)C>[NH2:23][C:22]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][OH:1])=[CH:5][CH:6]=2)[C:11]([CH3:20])=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:21]=1

참가 물질

4

반응물 2

HCID 9864CyanamideHCID 222913492-{[4-(2-Hydroxyethyl)phenyl]amino}-1-phenyl-1-propanone

생성물 1

HCID 222913562-[4-(2-amino-5-methyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethanol수율 33.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-{[4-(2-hydroxyethyl)phenyl]amino}-1-phenyl-1-propanone (1.3 g, 5.0 mmol) and cyanamide (420 mg, 10 mmol) in ethanol (60 mL) was refluxed for 16 h. After removal of solvent, the residue was diluted with dichloromethane. The organic layer was washed with water, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/ethanol (10:1) to give 490 mg (33%) of the title compound as yellow solids: 1H-NMR (CDCl3) δ 2.16 (3H, s), 2.96 (2H, t, J=5.6 Hz), 3.96 (2H, t, J=5.6 Hz), 4.24 (1H, br), 7.29-7.21 (2H, m), 7.46-7.38 (4H, m), 7.66-7.63 (2H, m).

후처리

  1. temperaturewas refluxed for 16 h
  2. customAfter removal of solvent
  3. additionthe residue was diluted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/ethanol (10:1)

출처 및 근거

ORD 기록
ord-d09fb717b79d46d3afa64cdcd2f4be1c
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956050B2

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