Ethacrynic Acid → 2,3-Dichloro-4-[4-(dimethylaminocarbonyl)-6-ethyl-3-oxo-1-cyclohexen-1-yl]phenoxy-acetic acid
Reaction equation
[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]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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).
Workup
- temperatureat reflux for 4 hours
- temperaturecooled
- concentrationconcentrated
- extractionextracted with chloroform
- washThe organic extracts were washed with water
- concentrationconcentrated
- customThe residue was recrystallized from acetonitrile
- additionfrom a mixture of water and acetic acid
Sources & evidence
- ORD record
- ord-6a002b8a6c3c4458b409eaab656b824b
- Source dataset
- uspto-grants-1988_01
- Patent number
- US04719310
Reaction notes
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