Water → N-(5-Nitro-pyrimidin-2-yl)-benzamide

HRID 714576

Reaction equation

HRID 714576 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.O>N1C=CC=CC=1>[C:11]([NH:1][C:2]1[N:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 764905-Nitropyrimidin-2-amine

Product 1

HCID 57699955N-(5-Nitro-pyrimidin-2-yl)-benzamideYield 45.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To stirred solution of 2-amino-5-nitropyrimidine (1.0 g, 7.14 mmol) in pyridine (20 ml) was added benzoyl chloride (0.92 ml, 7.93 mmol). The mixture was refluxed for 4 hr under nitrogen atmosphere. The reactant mixture was cooled to the room temperature and poured into 200 ml water. The resulting mixture was stirred overnight and then filtered in vacuo. The filter cake was washed with water (20 ml*3) and dried in vacuo to give 2-(N-benzoyl)amino-5-nitropyrimidine as a white solid (790 mg).

Workup

  1. temperatureThe mixture was refluxed for 4 hr under nitrogen atmosphere
  2. filtrationfiltered in vacuo
  3. washThe filter cake was washed with water (20 ml*3)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4703bc90db2a4c779ad15f3d7b8b4ead
Source dataset
uspto-grants-2015_11
Patent number
US09187458B2

Linked notes

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