4-Aminobenzonitrile → HCID 15005402, compound

HRID 973474Notes

Reaction equation

HRID 973474 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-b6d5b2fc98d14e8e9e273589bb66814a
Source dataset
uspto-grants-1991_11
Patent number
US05063237

Reaction notes

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