m-Chloroperbenzoic acid → HCID 178448800, compound

HRID 964847Notes

Reaction equation

HRID 964847 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])[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][C:9]([CH3:10])([CH3:12])[CH3:11])[CH:5]=[C:4]([Cl:13])[N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19073890HCID 19073890, compound

Product 1

HCID 178448800HCID 178448800, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

9 g of 2-amino-4-tert-butylamino-6-chloropyrimidine are suspended in 90 ml of ethanol. 24.70 g of meta-chloroperbenzoic acid are added dropwise as solution in 250 ml of ethanol. The reaction mixture is stirred at room temperature for 7 hours 30 minutes. It is evaporated to dryness. The residue is taken up in 100 ml of water. The pH is adjusted to 1 by adding concentrated hydrochloric acid. After 1 hour's stirring the precipitate is filtered off on sintered glass and then discarded. The filtrates are adjusted to pH 8 by adding concentrated sodium hydroxide and are then extracted with 3×100 ml of dichloromethane. The organic phase is separated off, dried over sodium sulfate, filtered on paper and evaporated to dryness. The residue obtained is recrystallized from 60 ml of acetonitrile. 1.30 g of 2-amino-4-tert-butylamino-6-chloropyrimidine 3-oxide are obtained.

Workup

  1. customIt is evaporated to dryness
  2. additionby adding concentrated hydrochloric acid
  3. stirringAfter 1 hour's stirring the precipitate
  4. filtrationis filtered off on sintered glass
  5. additionby adding concentrated sodium hydroxide
  6. extractionare then extracted with 3×100 ml of dichloromethane
  7. customThe organic phase is separated off
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered on paper
  10. customevaporated to dryness
  11. customThe residue obtained
  12. customis recrystallized from 60 ml of acetonitrile

Sources & evidence

ORD record
ord-62cb4356eb224772a369c535331954ba
Source dataset
uspto-grants-1998_06
Patent number
US05772990

Reaction notes

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