m-Chloroperbenzoic acid → HCID 178448801, compound

HRID 128929Notes

Reaction equation

HRID 128929 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[C:4]([Cl:13])[N:3]=1.ClC1C=CC=C(C(OO)=[O:22])C=1>C(O)C>[NH2:1][C:2]1[N+:7]([O-:22])=[C:6]([NH:8][CH2:9][CH:10]([CH3:11])[CH3:12])[CH:5]=[C:4]([Cl:13])[N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 2358976-Chloro-N~4~-(2-methylpropyl)pyrimidine-2,4(1H,3H)-diimine

Product 1

HCID 178448801HCID 178448801, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

34.70 g of 2-amino-4-isobutylamino-6-chloropyrimidine are dissolved in 250 ml of ethanol. 81.50 g of metachloroperbenzoic acid, in solution in 350 ml of ethanol, are added dropwise and while keeping the temperature of the reaction mixture at 20° C. After stirring for 2 h 30 min, the precipitate formed is filtered on sintered glass, washed with 100 ml of ethyl ether and then taken up in 100 ml of water. The pH is adjusted to 8 by addition of concentrated sodium hydroxide solution. After stirring for 1 hour, the precipitate is filtered on sintered glass, washed with 3×50 ml of water and dried under vacuum over phosphorus pentoxide at 50° C. 11.30 g of 2-amino-4-isobutylamino-6-chloropyrimidine 3-oxide are obtained.

Workup

  1. customat 20° C
  2. customthe precipitate formed
  3. filtrationis filtered on sintered glass
  4. washwashed with 100 ml of ethyl ether
  5. additionThe pH is adjusted to 8 by addition of concentrated sodium hydroxide solution
  6. stirringAfter stirring for 1 hour
  7. filtrationthe precipitate is filtered on sintered glass
  8. washwashed with 3×50 ml of water
  9. dry with materialdried under vacuum over phosphorus pentoxide at 50° C

Sources & evidence

ORD record
ord-ee8193695de54b5f9c9065284218828d
Source dataset
uspto-grants-1995_11
Patent number
US05466694

Reaction notes

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