Hydrochloric Acid → 5-chloro-N-(2-chlorophenyl)pyridine-2-carboxamide

HRID 509575Notes

Reaction equation

HRID 509575 reaction equation
NNC(=[N:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])C1C=CC(S(C)(=O)=O)=CC=1.[O:22]=S(Cl)Cl.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH2:33].C(N(CC)CC)C.Cl>C(Cl)Cl.C(OCC)(=O)C>[Cl:21][C:16]1[CH:17]=[CH:18][C:19]([C:20]([NH:33][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[Cl:26])=[O:22])=[N:14][CH:15]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 72402-ChloroanilineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 67958481N-amino-N'-(2-chlorophenyl)-4-methylsulfonyl-benzamidine

Product 1

HCID 679591095-chloro-N-(2-chlorophenyl)pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-chloropyridine-2-carboxylic acid 5 (1.0 g, 6.35 mmol) and SOCl2 (2.4 mL) in DCM (10 mL) was stirred for 2 hours and concentrated. The residue was dissolved in DCM (20 mL). To the solution was added 2-chlorobenzenamine (1.0 g, 7.84 mmol) and then triethylamine (2.0 mL, 14.43 mmol). The reaction mixture was stirred overnight at ambient temperature and ethyl acetate (50 mL) was added followed by 1N HCl (10 mL). The organic phase was washed with water and brine, dried and concentrated under reduced pressure to yield a light yellow solid. Yield: 0.8 g, 47%. 5-chloro-N-(2-chlorophenyl)pyridine-2-carboxamide 6 was used for the next step without further purification.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in DCM (20 mL)
  3. stirringThe reaction mixture was stirred overnight at ambient temperature
  4. washThe organic phase was washed with water and brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto yield a light yellow solid
  8. custom5-chloro-N-(2-chlorophenyl)pyridine-2-carboxamide 6 was used for the next step without further purification

Sources & evidence

ORD record
ord-5cc99d21194e443b84136ead0abf0d88
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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