Isopropylamine → Iprymidam

HRID 2398541Notes

Reaction equation

HRID 2398541 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH:10]([NH2:13])([CH3:12])[CH3:11].[OH-].[Na+]>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([NH:13][CH:10]([CH3:12])[CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 4867467Iprymidam

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

600 g of 2-amino-4,6-dichloro-pyrimidine (3.66 mols) are added to 3000 cc of alcohol, 395 g of isopropylamine (8.05 mols) are added, and the mixture is slowly heated to 80° during the course of 2 hours while stirring. After the material is dissolved, the solution is heated under reflux for 3 hours. The alcohol is then distilled off and the residue dissolved in dilute sulphuric acid. The solution must give a clearly acid reaction. The solution is shaken out several times with chloroform. A layer of 3000 cc of chloroform is subsequently placed under the aqueous solution and the solution is made alkaline with a caustic soda solution (pH 11), whereby the temperature should not exceed 35°. After shaking out the chloroform phase is separated and the aqueous phase is again shaken out with chloroform. The combined chloroform solution is dried with Glauber's salt after washing with water and the chloroform is evaporated. After standing for a short time, the oily residue crystallizes. The product may be recrystallized as described in Example 1 for purposes of purification.

Workup

  1. additionare added
  2. temperaturethe mixture is slowly heated to 80° during the course of 2 hours
  3. dissolutionAfter the material is dissolved
  4. temperaturethe solution is heated
  5. temperatureunder reflux for 3 hours
  6. distillationThe alcohol is then distilled off
  7. dissolutionthe residue dissolved in dilute sulphuric acid
  8. customThe solution must give
  9. customa clearly acid reaction
  10. customexceed 35°
  11. customis separated
  12. stirringthe aqueous phase is again shaken out with chloroform
  13. dry with materialThe combined chloroform solution is dried with Glauber's salt
  14. washafter washing with water
  15. customthe chloroform is evaporated
  16. customthe oily residue crystallizes
  17. customThe product may be recrystallized
  18. customas described in Example 1 for purposes of purification

Sources & evidence

ORD record
ord-5eeeb2ec4ca3443c8e84c9c029b14687
Source dataset
uspto-grants-1977_05
Patent number
US04025515

Reaction notes

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