Hydrogen Peroxide → 5-[7-(4-Carbamylphenoxy)heptyl]-3-methylisoxazole

HRID 544615Notes

Reaction equation

HRID 544615 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[O:19][N:18]=[C:17]([CH3:20])[CH:16]=2)=[CH:5][CH:4]=1)#[N:2].OO.[OH-].[Na+].S(=O)(=O)(O)[OH:28]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[O:19][N:18]=[C:17]([CH3:20])[CH:16]=2)=[CH:21][CH:22]=1)(=[O:28])[NH2:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 52712085-[7-(4-Cyanophenoxy)heptyl]-3-methylisoxazole

Product 1

HCID 133169625-[7-(4-Carbamylphenoxy)heptyl]-3-methylisoxazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 4.47 g (0.015 mole) of 5-[7-(4-cyanophenoxy)heptyl]-3-methylisoxazole (Example 5), 8 ml of 30% hydrogen peroxide, 8 ml of 95% ethanol and 0.6 ml of 6 N sodium hydroxide was stirred for ten minutes. There was then added 10 ml of 95% ethanol and the reaction mixture was warmed at 40°-50° C. for 4.5 hours, then held at room temperature overnight and treated with 5% sulfuric acid to neutral pH. The mixture was cooled and the solid product collected by filtration to give 4.4 g of 5-[7-(4-carbamylphenoxy)heptyl]-3-methylisoxazole, m.p. 153°-154° C., and recrystallized from methanol.

Workup

  1. temperaturethe reaction mixture was warmed at 40°-50° C. for 4.5 hours
  2. temperatureThe mixture was cooled
  3. filtrationthe solid product collected by filtration

Sources & evidence

ORD record
ord-834e4cc88f2b4f67ace134d6732022f0
Source dataset
uspto-grants-1984_05
Patent number
US04451476

Reaction notes

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