Hydrogen Peroxide → 3-(3-Bromopropyl)benzamide

HRID 1975285Notes

Reaction equation

HRID 1975285 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]#[N:12])[CH:8]=[CH:9][CH:10]=1.C(=O)(O)[O-:14].[K+].OO.O>CO.C(=O)([O-])[O-].[K+].[K+]>[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[C:11]([NH2:12])=[O:14]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 516893Potassium BicarbonateHCID 193772303-(3-Bromopropyl)benzonitrile

Product 1

HCID 193772323-(3-Bromopropyl)benzamideYield 298.9%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 887MethanolSolvent

Procedure

To 15.2 g (0.067 mole) of 3-(3-bromopropyl)cyanobenzene (the product of step (c)) in 55 ml methanol, 2.2 g potassium bicarbonate was added; to that mixture, 15.2 ml of 30% hydrogen peroxide was added dropwise. The reaction mixture was stirred for about 45 minutes. Then, 113 mg potassium carbonate was added the resulting mixture was stirred overnight. Water (about 35 ml) was added to the reaction mixture and the resulting solution put in a freezer for about 50 minutes. The solid was collected by filtration and dried overnight to give 15.9 g of the above-identified product as a solid, melting point 109° C.

Workup

  1. stirringwas stirred overnight
  2. waitthe resulting solution put in a freezer for about 50 minutes
  3. filtrationThe solid was collected by filtration
  4. customdried overnight

Sources & evidence

ORD record
ord-8580f0c0adaa4865847409f1a4c1f7a5
Source dataset
uspto-grants-1994_02
Patent number
US05286252

Reaction notes

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