3-Phenoxyaniline → Methyl 3-[[(3-phenoxyphenyl)amino]methyl]benzoate

HRID 50490

反応式

HRID 50490 の反応式
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[O:13]([C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1CCCCC1.O.C(Cl)Cl>[O:13]([C:20]1[CH:21]=[C:22]([NH:23][CH2:2][C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])[CH:24]=[CH:25][CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

6

反応物 2

HCID 771353-PhenoxyanilineHCID 517981Methyl 3-(bromomethyl)benzoate

生成物 1

HCID 23506109Methyl 3-[[(3-phenoxyphenyl)amino]methyl]benzoate収率 60%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8078Cyclohexane溶媒

実験手順

EX-612A) Methyl 3-(bromomethyl)benzoate (7.2 g, 0.031 mol) was added dropwise to a solution of 3-phenoxyaniline (20.5 g, 0.11 mol) in 160 mL of cyclohexane. The reaction mixture was refluxed overnight then cooled to room temperature and diluted with water and methylene chloride. The layers were separated, and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give a dark oil. The crude product was purified by reverse phase HPLC eluting with 20% to 90% acetonitrile in water to afford 6.2 g (59%) of the desired methyl 3-[[(3-phenoxyphenyl)amino]methyl]benzoate product as a yellow oil. ESMS m/z=334 [M+H]+.

後処理

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with methylene chloride
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give a dark oil
  8. customThe crude product was purified by reverse phase HPLC
  9. washeluting with 20% to 90% acetonitrile in water

出典と根拠

ORDレコード
ord-7be87054bbfb41eca817d15373a0a048
出典データセット
uspto-grants-2004_03
特許番号
US06710089B2

関連ノート

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