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

HRID 83779

반응식

HRID 83779 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-41e165b56fd94218afb2d5fb43b75aa8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846845B2

연결된 노트

불러오는 중…