Water → HCID 18978026, compound

HRID 1491570Notes

Reaction equation

HRID 1491570 reaction equation
[CH:1]1([C:4](=[O:29])[C:5](=[CH:25]OCC)[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:7])[CH2:3][CH2:2]1.Cl.[NH2:31]O.C([O-])(=O)C.[Na+].O>C(O)C>[CH:1]1([C:4]2[O:29][N:31]=[CH:25][C:5]=2[C:6](=[O:7])[C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 53807424HCID 53807424, compound

Product 1

HCID 18978026HCID 18978026, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3-cyclopropyl-2-ethoxymethylene-1-(2-phenylsulphenyl-4-trifluoromethylphenyl)propan-1,3-dione (7 g), hydroxylamine hydrochloride (1.24 g) and sodium acetate (1.5 g) in ethanol was stirred at 25° C. for 2 hours. The mixture was then poured into water and extracted with ethyl acetate. The solution was dried over anhydrous sodium sulphate and filtered. The filtrate was evaporated and the residue purified by column chromatography on silica, using a mixture of ethyl acetate and hexane as eluent. The resulting solution was evaporated and the residue crystallized from cyclohexane to give 3.06 g of 5-cyclopropyl-4-(2-phenylsulphenyl-4-trifluoromethylbenzoyl)isoxazole (compound 1), m.p. 115° C.

Workup

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

Sources & evidence

ORD record
ord-f73eea5cf1f74e8b92605ba8c5747561
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

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