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

HRID 589557Notes

Reaction equation

HRID 589557 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[N:8]=1>C(O)(C)C>[Cl:3][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178510036HCID 178510036, compound

Product 1

HCID 111955954-((4-Chloropyrimidin-2-yl)amino)benzonitrileYield 74.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Phosphorous oxychloride (104 gm) was added slowly to 4-(4-hydroxypyrimidin-2-ylamino)benzonitrile (12 gm) at 0° C. and then heated to reflux for 1 hour. The solution was then cooled to room temperature, stirred for 30 minutes and filtered. The precipitated solid thus obtained was dissolved in isopropyl alcohol at 0 to 5° C. and stirred for 1 hour at 0 to 5° C. The solid obtained was collected by filtration and then dried to obtain 9.75 gm of 4-(4-chloropyrimidin-2-ylamino)benzonitrile.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. filtrationfiltered
  4. customThe precipitated solid thus obtained
  5. stirringstirred for 1 hour at 0 to 5° C
  6. customThe solid obtained
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-9484418e6ac9449abf6b30ca4722f726
Source dataset
uspto-grants-2016_01
Patent number
US09233935B2

Reaction notes

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