Benzoyl chloride → N-(5-Nitro-pyrimidin-2-yl)-benzamide

HRID 1686004Notes

Reaction equation

HRID 1686004 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[N+:8]([C:5]1[CH:4]=[N:3][C:2]([NH:1][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:7][CH:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 764905-Nitropyrimidin-2-amine

Product 1

HCID 57699955N-(5-Nitro-pyrimidin-2-yl)-benzamideYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-5-nitropyrimidine (6.34 g, 45.3 mmol) in pyridine (100 ml) was added benzoyl chloride (5.8 ml, 49.8 mmol, 1.1 eq) dropwise over 10 minutes. The reaction mixture was refluxed for 6 hours, poured into ice (800 ml) and allowed to stand overnight. A brown solid was collected by filtration, washed with water and taken up in DCM (500 ml). The solution was washed with brine (3×200 ml), dried (MgSO4), filtered and concentrated under reduced pressure to leave a brown solid. Purification by column chromatography (1% methanol in DCM), afforded the title compound as a thick yellow oil (5.14 g, 47% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. filtrationA brown solid was collected by filtration
  3. washwashed with water
  4. washThe solution was washed with brine (3×200 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto leave a brown solid
  9. customPurification by column chromatography (1% methanol in DCM)

Sources & evidence

ORD record
ord-171dcef06837423d939b7c5895e5169b
Source dataset
uspto-grants-2012_04
Patent number
US08148531B2

Reaction notes

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