Acetaminophen → 2-(4-Acetylamino-phenoxy)-propionic acid methyl ester

HRID 83779

反応式

HRID 83779 の反応式
[NH:1]([C:5]1[CH:11]=[CH:10][C:8]([OH:9])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].C([O-])([O-])=O.[K+].[K+].[I-].[Na+].Cl[CH:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23]>CC(C)=O>[CH3:25][O:24][C:22](=[O:23])[CH:21]([O:9][C:8]1[CH:10]=[CH:11][C:5]([NH:1][C:2](=[O:3])[CH3:4])=[CH:6][CH:7]=1)[CH3:26]

参加物

6

反応物 4

HCID 1983AcetaminophenHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 28659Methyl 2-chloropropionate

生成物 1

HCID 549413982-(4-Acetylamino-phenoxy)-propionic acid methyl ester収率 27,257.9%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a mixture of paracetamol (150 g, 992 mmol), anhydrous K2CO3 (540 kg, 3.91 mol) and sodium iodide (18 gm, 120 mmol) in anhydrous acetone (3 L) was added methyl 2-chloropropionate (180 g, 1.469 mmol) and refluxed for 80 hours. The acetone was distilled off and water (3 L) was added. Crude 8 was extracted into chloroform, dried over Na2SO4, distilled and hexane (750 ml) was added. The solids were then filtered and recrystallised in methanol to give pure 8 (95 g, 40.4%) as a white powder with an m.p between 96.5-98.2° C.

後処理

  1. temperaturerefluxed for 80 hours
  2. distillationThe acetone was distilled off
  3. additionwater (3 L) was added
  4. extractionCrude 8 was extracted into chloroform
  5. dry with materialdried over Na2SO4
  6. distillationdistilled
  7. additionhexane (750 ml) was added
  8. filtrationThe solids were then filtered
  9. customrecrystallised in methanol

出典と根拠

ORDレコード
ord-41e165b56fd94218afb2d5fb43b75aa8
出典データセット
uspto-grants-2014_09
特許番号
US08846845B2

関連ノート

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