O-((2E)-3-Chloro-2-propen-1-yl)hydroxylamine → 2-[(E)-N-(3-chloroprop-2-enoxy)-C-ethylcarbonimidoyl]-5-(2-methylpyrazol-3-yl)cyclohexane-1,3-dione
Reaction equation
[CH3:1][N:2]1[C:6]([CH:7]2[CH2:12][C:11](=[O:13])[CH:10]([C:14](=O)[CH2:15][CH3:16])[C:9](=[O:18])[CH2:8]2)=[CH:5][CH:4]=[N:3]1.[Cl:19]/[CH:20]=[CH:21]/[CH2:22][O:23][NH2:24]>>[Cl:19][CH:20]=[CH:21][CH2:22][O:23]/[N:24]=[C:14](/[CH:10]1[C:11](=[O:13])[CH2:12][CH:7]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)[CH2:8][C:9]1=[O:18])\[CH2:15][CH3:16]Participants
3
Procedure
To 5 ml of an ethanolic solution of 0.35 g (1.4 mmols) of 5-(1-methyl-1H-pyrazol-5-yl)-2-propionylcyclohexane-1,3-dione was added 3.8 ml (1.4 mmols) of 0.38 mol ethanolic solution of (E)-3-chloro-2-propenyloxyamine. The mixture was reacted for 10 hours with stirring. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=b 1:2) to give 0.25 g of the product.
Workup
- customThe mixture was reacted for 10 hours
- customAfter completion of the reaction
- concentrationthe reaction mixture was concentrated under reduced pressure
- customThe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=b 1:2)
Sources & evidence
- ORD record
- ord-5531e9712f6d42a1ab5f13ad87a3c89a
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04863504
Reaction notes
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