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

HRID 2413840ノート

反応式

HRID 2413840 の反応式
[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]

参加物

5

反応物 3

HCID 3278Ethacrynic AcidHCID 16278DimethylacetoacetamideHCID 5360545Sodium

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6a002b8a6c3c4458b409eaab656b824b
出典データセット
uspto-grants-1988_01
特許番号
US04719310

反応ノート

読み込み中…