2-Chlorobenzoyl chloride → HCID 69520520, compound

HRID 1767744Notes

Reaction equation

HRID 1767744 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][C:12]1[N:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][C:12]1[N:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1)=[O:5]

Participants

4

Reactant 2

HCID 691102-Chlorobenzoyl chlorideHCID 764905-Nitropyrimidin-2-amine

Product 1

HCID 69520520HCID 69520520, compoundYield 43,782.301%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-chlorobenzoyl chloride (577 mg, 3.3 mmol) was added dropwise to a stirred suspension of 2-amino-5-nitropyrimidine (420 mg, 3 mmol) in pyridine (5 ml) and the reaction was heated at reflux for 4 hours under an inert atmosphere followed by solvent removed in vacuo. Purification by flash chromatography on silica gel, eluting with 10–60% ethyl acetate in hexane yielded 2-(N-2-chlorobenzoyl)amino-5-nitropyrimidine (366 g, 44% yield) as a beige solid:

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4 hours under an inert atmosphere
  3. customremoved in vacuo
  4. customPurification by flash chromatography on silica gel
  5. washeluting with 10–60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-528dceffc331427cb2f0306dbee576b9
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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