Hydroxyamine hydrochloride → HCID 22342446, compound

HRID 1383267Notes

Reaction equation

HRID 1383267 reaction equation
[CH3:1][S:2][C:3](SC)=[C:4]([C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[S:22]([CH3:25])(=[O:24])=[O:23])=[O:11])[C:5]([CH:7]1[CH2:9][CH2:8]1)=[O:6].Cl.[NH2:29]O.C([O-])(=O)C.[Na+]>ClCCl.C(O)C>[CH:7]1([C:5]2[O:6][N:29]=[C:3]([S:2][CH3:1])[C:4]=2[C:10](=[O:11])[C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[S:22]([CH3:25])(=[O:24])=[O:23])[CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochloride3×HCID 517045Sodium Acetate3×HCID 54454488HCID 54454488, compound

Product 1

HCID 22342446HCID 22342446, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 12.5 g (28.4 mmol) 2-(bis-methylsulfanylmethylene)-1 -cyclopropyl-3-(2-methanesulfonyl-4-trifluoromethylphenyl)propane-1,3-dione in 80 ml dichloromethane, 140 ml each of ethanol, 2.82 g (39.8 mmol) hydroxylamine hydrochloride and 3.4 g (41.2 mmol) anhydrous sodium acetate is successively added. The reaction mixture is then agitated for 48 hours at a temperature of 20° C. Then 50 ml dichloromethane, 50 ml ethanol, 1.4 g hydroxylamine hydrochloride and 1.7 g anhydrous sodium acetate are added, and the mixture is agitated for a further 3 days at 20° C. The reaction mixture is subsequently heated to a temperature of 30° C., and 2.8 g hydroxylamine hydrochloride and 3.4 g sodium acetate are added. After 18 hours' agitation at a temperature of 30° C., the solvents are distilled off and the residue taken up in 300 ml ethyl acetate. The organic phase is washed twice with water and once with concentrated aqueous sodium chloride solution. After the organic phase has been dried over sodium sulfate, it is treated with activated charcoal, filtered and evaporated to dryness. After recrystallization from a little diisopropylether, 10.7 g 5-cyclopropyl-3-methylsulfanyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)isoxazole is obtained in the form of crystalline solid matter with a melting point of 145-146° C.

Workup

  1. stirringthe mixture is agitated for a further 3 days at 20° C
  2. additionare added
  3. waitAfter 18 hours' agitation at a temperature of 30° C.
  4. distillationthe solvents are distilled off
  5. washThe organic phase is washed twice with water and once with concentrated aqueous sodium chloride solution
  6. dry with materialAfter the organic phase has been dried over sodium sulfate, it
  7. additionis treated with activated charcoal
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customAfter recrystallization from a little diisopropylether

Sources & evidence

ORD record
ord-69ceff90975f474ab36aaf24f94a7448
Source dataset
uspto-grants-2001_07
Patent number
US06255251B1

Reaction notes

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