Ethanol → HCID 54302995, compound

HRID 863394Notes

Reaction equation

HRID 863394 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:19])[C:9](=[CH:15][N:16](C)C)[C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[C:4]([S:20][CH3:21])[C:3]=1[F:22].O.[CH2:24]([OH:26])[CH3:25]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:19])[CH:9]([CH:15]=[N:16][O:26][CH2:24][CH3:25])[C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[C:4]([S:20][CH3:21])[C:3]=1[F:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 962WaterHCID 53929884HCID 53929884, compound

Product 1

HCID 54302995HCID 54302995, compound

Conditions

Temperature
25 °C

Procedure

A mixture of 1-(4-chloro-3-fluoro-2-methylsulphenylphenyl)-3-cyclopropyl-2-(dimethylaminomethylene)-propan-1,3-dione (3 g) and O-ethylhydroxylaminehydrochloride (1 g) in ethanol (20 ml) was stirred at 25° C. for 2 hours. The mixture was poured into water and extracted with dichloromethane. The solution was dried (anhydrous sodium sulphate) and filtered. The filtrate was evaporated and the mixture purified by column chromatography on silica, using a mixture of ethyl acetate and hexane as eluent. The resulting solution was evaporated and 1-(4-chloro-3-fluoro-2-methylsulphenylphenyl)-3-cyclopropyl-2-(ethoxyiminomethyl)-propan-1,3-dione (compound 5) was obtained as a reddish gum (2.4 -g), NMR (CDCl3) δ 1.1-1.4(m, 7H), 2.7(m, 1H), 2.4(s, 3H), 3.9(m, 2H), 7.0(m, 1H), 7.3(m, 1H), 7.6(s, 1H), 17.4(s, 1H) ppm.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe solution was dried (anhydrous sodium sulphate)
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe mixture purified by column chromatography on silica
  6. additiona mixture of ethyl acetate and hexane as eluent
  7. customThe resulting solution was evaporated

Sources & evidence

ORD record
ord-0e2f89b880114fe3b15a191a5f515108
Source dataset
uspto-grants-1998_02
Patent number
US05721193

Reaction notes

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