4-Fluoroiodobenzene → 1-(4-fluorophenyl)-3-(2-hydroxyethyl)-2(3H)-benzimidazolone

HRID 1290786

반응식

HRID 1290786 반응식
[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13].[F:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-]>[O-2].[Zn+2].O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:6]2[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:4]([CH2:3][CH2:2][OH:1])[C:5]2=[O:13])=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 96054-FluoroiodobenzeneHCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 41574231-(2-Hydroxyethyl)-1H-benzo[d]imidazol-2(3H)-one

생성물 1

HCID 232826611-(4-fluorophenyl)-3-(2-hydroxyethyl)-2(3H)-benzimidazolone수율 14.5%

시약·촉매·용매 2

HCID 3007857Zinc Oxide촉매HCID 962Water용매

실험 절차

A mixture of 1-(2-hydroxyethyl)benzimidazolone (J. Davoll, J. Chem. Soc., 1960, 308) (9 g), 4-fluoroiodobenzene (23 g), potassium carbonate (8.0 g), cupper(I) iodide (1 g), and zinc oxide (0.5 g) in N-methyl-2(3H)-pyrrolidinone (100 ml) was kept at 155° C. for 4.5 h. After cooling water (500 ml) was added followed by extraction with ethyl acetate (3×200 ml). The organic phase was washed with water and saturated calcium chloride solution and dried over magnesium sulfate. Removal of solvent in vacuo gave an oil which was purified by chromatography (silica gel, ethyl acetate) giving 1-(4-fluorophenyl)-3-(2-hydroxyethyl)-2(3H)-benzimidazolone (2 g) as a solid, mp: 124°-26° C.

후처리

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate (3×200 ml)
  3. washThe organic phase was washed with water and saturated calcium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of solvent in vacuo
  6. customgave an oil which
  7. customwas purified by chromatography (silica gel, ethyl acetate)

출처 및 근거

ORD 기록
ord-a7520fd548084caeaa1dda9e18c00fe4
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753661

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