Hydrochloric Acid → Methyl [3-bromo-4-(3-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

HRID 660881ノート

反応式

HRID 660881 の反応式
[Br:1][C:2]1[N:3]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[C:4](=[O:7])[NH:5][N:6]=1.Cl[CH2:17][C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C.C(OCC)(=O)C>[CH3:21][O:20][C:18](=[O:19])[CH2:17][N:5]1[C:4](=[O:7])[N:3]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[C:2]([Br:1])=[N:6]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 580120875-bromo-4-(3-fluorobenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

生成物 1

HCID 58011964Methyl [3-bromo-4-(3-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1.50 g (4.69 mmol) of the compound from Example 137A are stirred under reflux for 4 hrs together with 508 mg (4.69 mmol) of methyl chloroacetate and 1.30 g (9.4 mmol) of potassium carbonate in 33 ml acetonitrile. After cooling, the mixture is neutralized with 1 N hydrochloric acid and diluted with ethyl acetate. The organic phase is separated, washed with saturated sodium chloride solution, dried over sodium sulphate and freed of the volatile components on the rotary evaporator. The residue is dissolved in 20 ml dichloromethane and absorbed onto 3 g of diatomaceous earth. After removal of the solvent on the rotary evaporator the solid is transferred to a silica gel chromatography column and the product purified by elution with cyclohexane/ethyl acetate (gradient 5:1→1:1). 1.36 g (84% of theory) of the title compound are obtained.

後処理

  1. temperatureAfter cooling
  2. customThe organic phase is separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customfreed of the volatile components on the rotary evaporator
  6. dissolutionThe residue is dissolved in 20 ml dichloromethane
  7. customabsorbed onto 3 g of diatomaceous earth
  8. customAfter removal of the solvent
  9. customon the rotary evaporator the solid
  10. customthe product purified by elution with cyclohexane/ethyl acetate (gradient 5:1→1:1)

出典と根拠

ORDレコード
ord-359534aefba2463dbc1dfb4060510bda
出典データセット
uspto-grants-2011_12
特許番号
US08084481B2

反応ノート

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