4-Aminobenzonitrile → HCID 15005402, compound

HRID 892764Notes

Reaction equation

HRID 892764 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1>C(O)CCC>[NH2:1][C:2]1[C:7]([NH:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=[N:6][CH:5]=[N:4][C:3]=1[Cl:9]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 15005402HCID 15005402, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-amino-4,6-dichloropyrimidine (7.00 g, 42.7 mmol) and 4-aminobenzonitrile (5.04 g, 42.7 mmol) in n-butanol (130 ml) was heated at reflux for 16 hours. After cooling the mixture the solid which precipitated out was filtered off, and partitioned between dichloromethane (500 ml) and saturated aqueous sodium bicarbonate. The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the title compound (6.31 g, 60%).

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureAfter cooling the mixture the solid which
  3. customprecipitated out
  4. filtrationwas filtered off
  5. custompartitioned between dichloromethane (500 ml) and saturated aqueous sodium bicarbonate
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05c9a32fd42c44a2b21d71b3d06d84c3
Source dataset
uspto-grants-1992_06
Patent number
US05120747

Reaction notes

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