Chlorosuccinimide → HCID 178448814, compound

HRID 128930Notes

Reaction equation

HRID 128930 reaction equation
[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH:9][CH2:10][CH:11]([CH3:13])[CH3:12])[CH:5]=[C:4]([Cl:14])[N:3]=1.[Cl:15]N1C(=O)CCC1=O>C(O)C>[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH:9][CH2:10][CH:11]([CH3:12])[CH3:13])[C:5]([Cl:15])=[C:4]([Cl:14])[N:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178448801HCID 178448801, compound

Product 1

HCID 178448814HCID 178448814, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.30 g of 2-amino-4-isobutylamino-6-chloropyrimidine 3-oxide are suspended in 110 ml of ethanol. 4.85 g of N-chlorosuccinimide are added. The reaction mixture is heated under reflux for 2 hours and then evaporated to dryness. The residue is taken up in 50 ml of water. The pH is adjusted to 8 by addition of concentrated sodium hydroxide solution. The precipitate formed is filtered on sintered glass, washed with water until neutral and dried under vacuum over phosphorus pentoxide. It is recrystallized from 150 ml of ethanol. 4.30 g of 2-amino-4-isobutylamino-5,6-dichloropyrimidine 3-oxide are obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 2 hours
  3. customevaporated to dryness
  4. additionThe pH is adjusted to 8 by addition of concentrated sodium hydroxide solution
  5. customThe precipitate formed
  6. filtrationis filtered on sintered glass
  7. washwashed with water until neutral and
  8. dry with materialdried under vacuum over phosphorus pentoxide
  9. customIt is recrystallized from 150 ml of ethanol

Sources & evidence

ORD record
ord-85a90ae12d1043a7804ed8f3cde98523
Source dataset
uspto-grants-1995_11
Patent number
US05466694

Reaction notes

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