Ethyl 2-chloro-2-(hydroxyimino)acetate → Ethyl 5-[2-chloro-4(methylsulphenyl)phenyl]-4-cyclopropylcarbonylisoxazole-3-carboxylate

HRID 21445Notes

Reaction equation

HRID 21445 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]#[C:11][C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13].[CH3:17][CH2:18][O:19][C:20](/[C:22](/Cl)=[N:23]\[OH:24])=[O:21]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[O:24][N:23]=[C:22]([C:20]([O:19][CH2:18][CH3:17])=[O:21])[C:11]=1[C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13]

Participants

4

Reactant 2

HCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetateHCID 199317691-[2-Chloro-4-(methylsulphenyl)phenyl]-3-cyclopropylprop-1-yn-3-one

Product 1

HCID 19931784Ethyl 5-[2-chloro-4(methylsulphenyl)phenyl]-4-cyclopropylcarbonylisoxazole-3-carboxylateYield 35.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-[2-chloro-4-(methylsulphenyl)phenyl]-3-cyclopropylprop-1-yn-3-one (1.39g) and ethyl chloro-oximidoacetate (0.84g) in toluene was stirred and heated at reflux overnight. It was cooled and evaporated to dryness. The residue was purified by chromatography eluted with a mixture of hexane and dichloromethane, followed by ether to give ethyl 5-[2-chloro-4-(methylsulphenyl)phenyl]-4-cyclopropylcarbonylisoxazole-3-carboxylate (compound 9, 0.72g) as an orange solid, m.p. 50° C.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureIt was cooled
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography
  6. washeluted with a mixture of hexane and dichloromethane

Sources & evidence

ORD record
ord-d348c3517787435e86f08c4b1804691e
Source dataset
uspto-grants-1995_06
Patent number
US05424276

Reaction notes

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