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

HRID 1290786

反応式

HRID 1290786 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3007857Zinc Oxide触媒HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a7520fd548084caeaa1dda9e18c00fe4
出典データセット
uspto-grants-1998_05
特許番号
US05753661

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