Cyclohexylamine → 2,6-dichloro-N-cyclohexylnicotinamide

HRID 2424895Notes

Reaction equation

HRID 2424895 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-c785898829454c4d947edf1b619a8be0
Source dataset
uspto-grants-2011_06
Patent number
US07964618B2

Reaction notes

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