Cyclohexylamine → 2,6-dichloro-N-cyclohexylnicotinamide

HRID 1187356Notes

Reaction equation

HRID 1187356 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[CH:18]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[C:3]([C:4]([NH:24][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:6])=[CH:7][CH:8]=[C:9]([Cl:11])[N:10]=1

Participants

6

Reactant 3

HCID 7965CyclohexylamineHCID 65578Oxalyl chlorideHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 527624932,6-dichloro-N-cyclohexylnicotinamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,6-dichloronicotinic acid (5.005 g, 26.18 mmol) in DCM (60 ML) was added a few drops of DMF followed by the addition dropwise of oxalyl chloride (2.27 mL, 26.18 mmol). The reaction was stirred at room temperature for two hours until gas bubbling had stopped. The solvent was evaporated under reduced pressure to give an oil. DCM (60 mL) was added and the reaction mixture was cooled in an ice bath. Cyclohexylamine (5.98 mL, 52.36 mmol) was added slowly keeping the temperature below 15° C. The reaction was stirred at room temperature overnight.

Workup

  1. custombubbling
  2. customThe solvent was evaporated under reduced pressure
  3. customto give an oil
  4. temperaturethe reaction mixture was cooled in an ice bath
  5. customthe temperature below 15° C
  6. stirringThe reaction was stirred at room temperature overnight

Sources & evidence

ORD record
ord-c5a1a1c464f74476a090e3dd6b8b97ba
Source dataset
uspto-grants-2014_03
Patent number
US08673938B2

Reaction notes

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