Ethacrynic Acid → 2,3-Dichloro-4-[4-(dimethylaminocarbonyl)-6-ethyl-3-oxo-1-cyclohexen-1-yl]phenoxy-acetic acid

HRID 2413840노트

반응식

HRID 2413840 반응식
[CH3:1][N:2]([CH3:9])[C:3](=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].[Na].[Cl:11][C:12]1[C:22]([Cl:23])=[C:21]([C:24](=O)[C:25](=[CH2:28])[CH2:26][CH3:27])[CH:20]=[CH:19][C:13]=1[O:14][CH2:15][C:16]([OH:18])=[O:17]>C(O)C>[Cl:11][C:12]1[C:22]([Cl:23])=[C:21]([C:24]2[CH:25]([CH2:26][CH3:27])[CH2:28][CH:4]([C:3]([N:2]([CH3:9])[CH3:1])=[O:8])[C:5](=[O:6])[CH:7]=2)[CH:20]=[CH:19][C:13]=1[O:14][CH2:15][C:16]([OH:18])=[O:17]

참가 물질

5

반응물 3

HCID 3278Ethacrynic AcidHCID 16278DimethylacetoacetamideHCID 5360545Sodium

생성물 1

HCID 140764692,3-Dichloro-4-[4-(dimethylaminocarbonyl)-6-ethyl-3-oxo-1-cyclohexen-1-yl]phenoxy-acetic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

N,N-Dimethylacetoacetamide (13.7 g, 0.1062M) was added at 65° to a solution of sodium (2.44 g, 0.1062M) dissolved in ethanol (200 ml). After 3-5 minutes [2,3-dichloro-4-(2-methylenebutyryl)phenoxy]acetic acid (15.2 g, 0.05M) was added and the suspension was stirred at reflux for 4 hours, cooled and concentrated. The residue was taken up in water, acidified with hydrochloric acid and extracted with chloroform. The organic extracts were washed with water and concentrated. The residue was recrystallized from acetonitrile and then from a mixture of water and acetic acid to obtain 2,3-dichloro-4-[4-(dimethylaminocarbonyl)-6-ethyl-3-oxo-1-cyclohexen-1-yl]phenoxy-acetic acid, m.p. 211° (d).

후처리

  1. temperatureat reflux for 4 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. extractionextracted with chloroform
  5. washThe organic extracts were washed with water
  6. concentrationconcentrated
  7. customThe residue was recrystallized from acetonitrile
  8. additionfrom a mixture of water and acetic acid

출처 및 근거

ORD 기록
ord-6a002b8a6c3c4458b409eaab656b824b
출처 데이터셋
uspto-grants-1988_01
특허 번호
US04719310

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