m-Chloroperbenzoic acid → 4-Chloro-2,6-dimethylpyrimidine 1-oxide

HRID 1755651Notes

Reaction equation

HRID 1755651 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.ClC1C=CC=C(C(OO)=[O:18])C=1>ClCCl>[CH3:1][C:2]1[N+:7]([O-:18])=[C:6]([CH3:8])[CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 31541994-Chloro-2,6-dimethylpyrimidine

Product 1

HCID 126992254-Chloro-2,6-dimethylpyrimidine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

20 g (14.03×10-2 mol) of 2,4-dimethyl-6-chloropyrimidine are dissolved in 300 ml of dichloromethane in a 500 ml three-necked flask fitted with a thermometer and a magnetic stirrer. The mixture is cooled to 5° C. and 65.3 g of 55% metachloroperbenzoic acid, which is about 1.5 equivalents, are then added in solid portions. The reaction mixture is then stirred for 24 hours at ambient temperature (25° C.) and then filtered through a 3 frit. The filtrate is washed with 150 ml of a 6% aqueous sodium hydroxide solution and then with 2×50 ml of water to render neutral. It is then dried over sodium sulphate and then filtered through paper and evaporated. The crude mass is recrystallised from n-hexane.

Workup

  1. customfitted with a thermometer and a magnetic stirrer
  2. additionare then added in solid portions
  3. filtrationfiltered through a 3 frit
  4. washThe filtrate is washed with 150 ml of a 6% aqueous sodium hydroxide solution
  5. dry with materialIt is then dried over sodium sulphate
  6. filtrationfiltered through paper
  7. customevaporated
  8. customThe crude mass is recrystallised from n-hexane

Sources & evidence

ORD record
ord-8eb253211e7e4ba6b81072fad965b435
Source dataset
uspto-grants-1995_08
Patent number
US05438058

Reaction notes

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