Cyclohexanecarbonyl chloride → HCID 45086857, compound

HRID 1767742Notes

Reaction equation

HRID 1767742 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:10][C:11]1[N:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1>N1C=CC=CC=1.Cl>[CH:1]1([C:7]([NH:10][C:11]2[N:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 764905-Nitropyrimidin-2-amine

Product 1

HCID 45086857HCID 45086857, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

Cyclohexanoyl chloride (1.05 g, 7.14 mmol) was added dropwise to a stirred suspension of 2-amino-5-nitropyrimidine (1.0 g, 7.14 mmol) in pyridine (10 ml) and the reaction was heated at reflux for 4 hours under an inert atmosphere. The reaction mixture was cooled then stirred in 2N hydrochloric acid (100 ml) and extracted with ethyl acetate. Crystallisation from ethyl acetate/hexane, yielded 2-(N-cyclohexanoyl)amino-5-nitropyrimidine (1.15 g, 64% yield) as a beige solid:

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4 hours under an inert atmosphere
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate
  5. customCrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-40a49b38cf1046398c13ce9683ac2c53
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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