Sodium Carbonate → 5-Ethoxypyrimidine N-oxide

HRID 1647802Notes

Reaction equation

HRID 1647802 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[N:6][CH:7]=[N:8][CH:9]=1)[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:15].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:5]=[N:6][CH:7]=[N+:8]([O-:15])[CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 199216885-Ethoxypyrimidine

Product 1

HCID 450801615-Ethoxypyrimidine N-oxideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 5-ethoxypyrimidine (2.00 g, 16.1 mmol) in CH2Cl2 (100 mL) was added 3-chloroperoxybenzoic acid, 50-60% tech. grade, (6.13 g, 17.7 mmol) and the reaction stirred at 23° C. for 18 h. The reaction was extracted with water (2 mL) containing Na2CO3 (1.71 g, 16.1 mmol). The organic phase was dried with anhydrous K2CO3, filtered, and concentrated under reduced pressure to afford the N-oxide (1.75 g, 78%).

Workup

  1. extractionThe reaction was extracted with water (2 mL)
  2. dry with materialThe organic phase was dried with anhydrous K2CO3
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a03826c25264af6b7bcaeeccce013ad
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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