Sodium Hydroxide → HCID 178456788, compound

HRID 964854Notes

Reaction equation

HRID 964854 reaction equation
[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH:9][CH2:10][CH2:11][CH3:12])[CH:5]=[C:4]([N:13]([CH3:15])[CH3:14])[N:3]=1.[Cl:16]N1C(=O)CCC1=O.[OH-].[Na+]>C(O)C.O>[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH:9][CH2:10][CH2:11][CH3:12])[C:5]([Cl:16])=[C:4]([N:13]([CH3:15])[CH3:14])[N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 178456793HCID 178456793, compound

Product 1

HCID 178456788HCID 178456788, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

1 g of 2-amino-4-propylamino-6-dimethylamino-pyrimidine 3-oxide of Example 1 is dissolved in 15 ml of ethanol. 0.75 g of N-chlorosuccinimide are added as solution in 35 ml of ethanol, dropwise at room temperature. After 4 hours' stirring the reaction mixture is evaporated to dryness. The oil obtained is taken up in 10 ml of water. The pH is adjusted to 8 by adding sodium hydroxide and the mixture is then extracted with 3×20 ml of butanol. The butanol phase is evaporated to dryness. The residue is recrystallized from 5 ml of acetonitrile. 0.7 g of 2-amino-4-propylamino-5-chloro-6-dimethylaminopyrimidine 3-oxide are obtained.

Workup

  1. customis evaporated to dryness
  2. customThe oil obtained
  3. extractionthe mixture is then extracted with 3×20 ml of butanol
  4. customThe butanol phase is evaporated to dryness
  5. customThe residue is recrystallized from 5 ml of acetonitrile

Sources & evidence

ORD record
ord-f795c63eb54a495392245897d0564f84
Source dataset
uspto-grants-1998_06
Patent number
US05772990

Reaction notes

Loading…