Hydrogen Peroxide → 3-(4-Chlorophenyl)-7-methyl-2,1-benzisoxazole

HRID 1198995Notes

Reaction equation

HRID 1198995 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:10].OO>C(O)(=O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[O:10][N:1]=[C:2]3[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=23)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 15634752(2-Amino-3-methylphenyl)(4-chlorophenyl)methanone

Product 1

HCID 156347543-(4-Chlorophenyl)-7-methyl-2,1-benzisoxazoleYield 34%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 49 g (0.2 mole) of (2-amino-3-methylphenyl)(4-chlorophenyl)methanone, 1 liter of glacial acetic acid and 200 ml of 30% hydrogen peroxide was let stand at ambient temperature over the weekend. The mixture was heated on a steam bath for 1 hr and poured into 2.5 liters of ice water. The solid which precipitated was collected by filtration, washed with water, and recrystallized from 2-propanol and then from cyclohexane to yield 16.4 g (34%) of crystals, m.p. 134°-136° C.

Workup

  1. customwas let stand at ambient temperature over the weekend
  2. temperatureThe mixture was heated on a steam bath for 1 hr
  3. customThe solid which precipitated
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-9616ec7bec384bb5a8c4b0d6042bfc19
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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