Phosphorus oxychloride → 4-((4-Chloropyrimidin-2-yl)amino)benzonitrile

HRID 2108688Notes

Reaction equation

HRID 2108688 reaction equation
O[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178510036HCID 178510036, compound

Product 1

HCID 111955954-((4-Chloropyrimidin-2-yl)amino)benzonitrile

Procedure

A mixture of 4-[(4-hydroxy-2-pyrimidinyl)amino]-benzonitrile (0.12 mol) in POCl3 (90 ml) was stirred and refluxed under Argon for 20 minutes. The reaction mixture was slowly poured onto 750 ml ice/water, and the solid was separated by filtration. The solid was suspended in 500 ml water, and the pH of the suspension was adjusted to neutral by adding a 20% NaOH solution. The solid was again separated by filtration, suspended in 200 ml 2-propanone, and 1 L methylene chloride was added. The mixture was heated till all solid had dissolved. After cooling to room temperature, the aqueous layer was separated, and the organic layer was dried over magnesium sulfate. During removal of the drying agent by filtration, a solid formed in the filtrate. Further cooling of the filtrate in the freezer, followed by filtration, yielded 21.38 g of 4-[(4-chloro-2-pyrimidinyl)amino]-benzonitrile (intermediate 2).

Workup

  1. temperaturerefluxed under Argon for 20 minutes
  2. customthe solid was separated by filtration
  3. additionby adding a 20% NaOH solution
  4. customThe solid was again separated by filtration
  5. addition1 L methylene chloride was added
  6. temperatureThe mixture was heated till all solid
  7. dissolutionhad dissolved
  8. customthe aqueous layer was separated
  9. dry with materialthe organic layer was dried over magnesium sulfate
  10. customDuring removal of the drying agent
  11. filtrationby filtration
  12. customa solid formed in the filtrate
  13. temperatureFurther cooling of the filtrate in the freezer
  14. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-b23796bedbd44b17bde85fc9e28bbb7d
Source dataset
uspto-grants-2009_04
Patent number
US07514445B2

Reaction notes

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