N-Methylaniline → (Methyl-phenyl-amino)-acetic acid ethyl ester

HRID 352197

反応式

HRID 352197 の反応式
Br[CH2:2][CH2:3][O:4][C:5](=[O:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+].[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH2:3]([O:4][C:5](=[O:7])[CH2:6][N:15]([CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:2]

参加物

5

反応物 3

HCID 7515N-MethylanilineHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethane

生成物 1

HCID 265936(Methyl-phenyl-amino)-acetic acid ethyl ester収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of bromoethylacetate, 3.3 mL (30.0 mmol) in 100 mL of tetrahydrofuran was added 4.14 g (30.0 mmol) of potassium carbonate and 3.25 mL of N-methylaniline. The reaction mixture stirred overnight at rt. and was concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and saturated aqueous NaHCO3. The mixture was washed with saturated NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by column chromatography using EtOAc/hexanes as eluent and concentrated to dryness to give 4.74 g (82%) of the desired product as a tan oil. MS (ion spray) 194.1 (M+1).

後処理

  1. concentrationand was concentrated to dryness
  2. customThe residue was partitioned between 20% isopropanol/chloroform and saturated aqueous NaHCO3
  3. washThe mixture was washed with saturated NaHCO3
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by column chromatography
  9. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-2e69b577dcc348c98e5d4282115c8492
出典データセット
uspto-grants-2004_06
特許番号
US06743794B2

関連ノート

読み込み中…