Ammonia → 3(2H)-Isoxazolone, 4-methyl-5-phenyl-

HRID 1461223Notes

Reaction equation

HRID 1461223 reaction equation
[C:1]1([C:7]2[O:11][NH:10][C:9](=[O:12])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1(C)C=CC(S(OC)(=O)=O)=CC=1.[OH-].[Na+].N>O>[CH3:13][C:8]1[C:9](=[O:12])[NH:10][O:11][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6645Methyl p-toluenesulfonateHCID 14798Sodium HydroxideHCID 703183(2H)-Isoxazolone, 5-phenyl-

Product 1

HCID 38456533(2H)-Isoxazolone, 4-methyl-5-phenyl-Yield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To 60 g of 5-phenyl-3-isooxazolone was added 150 ml of methyl p-toluenesulfonate and the mixture obtained wa stirred for 3 hours at 80° C. The reaction mixture was allowed to cool, and after gradually adding thereto 30 ml of an aqueous 10% sodium hydroxide solution and 50 ml of an aqueous 30% ammonia solution under cooling, the resultant mixture was stirred for one hour at room temperature. Then, 500 ml of water was further added thereto and the mixture was stirred for a few hours at room temperature to deposit crystals, which were collected by filtration and dried to provide 30 g of the desired compound. The yield was 46%.

Workup

  1. customthe mixture obtained
  2. temperatureto cool
  3. additionafter gradually adding
  4. stirringthe mixture was stirred for a few hours at room temperature
  5. filtrationwere collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-55c6bcccc6374c9ca5580f92503f36b1
Source dataset
uspto-grants-1991_12
Patent number
US05075208

Reaction notes

Loading…