Phosphorus oxychloride → 2-Amino-4-chloro-6-(2,2-dichlorovinyl)pyrimidine

HRID 3908Notes

Reaction equation

HRID 3908 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH:8]=[C:9]([Cl:11])[Cl:10])[CH:5]=[C:4](O)[N:3]=1.P(Cl)(Cl)([Cl:15])=O>>[NH2:1][C:2]1[N:3]=[C:4]([Cl:15])[CH:5]=[C:6]([CH:8]=[C:9]([Cl:11])[Cl:10])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178418559HCID 178418559, compound

Product 1

HCID 201535042-Amino-4-chloro-6-(2,2-dichlorovinyl)pyrimidine

Procedure

10 Parts of 2-amino-4-(2,2-dichlorovinyl)-6-hydroxypyrimidine and 66 parts of phosphorus oxychloride were heated together under reflux for 1 hour with stirring. The solution was cooled and excess phosphorus oxychloride was removed in vacuo on a rotary evaporator. The residual viscous oil was poured onto ice, with stirring. Solid sodium bicarbonate was added portionwise until the solution had pH 7-8. The precipitated solid was filtered, washed with water and dried. Recrystallisation from aqueous methanol gave 2-amino-4-chloro-6-(2,2-dichlorovinyl)pyrimidine m.p. 119°-120° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureThe solution was cooled
  3. customexcess phosphorus oxychloride was removed in vacuo on a rotary evaporator
  4. additionThe residual viscous oil was poured onto ice
  5. stirringwith stirring
  6. additionSolid sodium bicarbonate was added portionwise until the solution
  7. filtrationThe precipitated solid was filtered
  8. washwashed with water
  9. customdried
  10. customRecrystallisation from aqueous methanol

Sources & evidence

ORD record
ord-2d0c936e376d46a4a7dfb16b647c8164
Source dataset
uspto-grants-1988_02
Patent number
US04723006

Reaction notes

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