Hydrochloric Acid → N-(2-chlorophenyl)-5-(methylsulfonyl)picolinamide

HRID 509586Notes

Reaction equation

HRID 509586 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C[Al](C)C.[CH3:13][S:14]([C:17]1[CH:18]=[CH:19][C:20]([C:23](OC)=[O:24])=[N:21][CH:22]=1)(=[O:16])=[O:15].Cl>C1(C)C=CC=CC=1.ClCCl>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:23](=[O:24])[C:20]1[CH:19]=[CH:18][C:17]([S:14]([CH3:13])(=[O:16])=[O:15])=[CH:22][N:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72402-ChloroanilineHCID 16682925TrimethylaluminumHCID 53429647Methyl 5-(methanesulfonyl)pyridine-2-carboxylate

Product 1

HCID 67958704N-(2-chlorophenyl)-5-(methylsulfonyl)picolinamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

2-Chloroaniline (1.20 g, 0.0093 mol) in toluene (20 mL) was added to trimethylaluminum (2.0 M 4.6 mL) then methyl 5-(methylsulfonyl)picolinate 4 (1.0 g, 4.65 mol) was added and the mixture was heated to 80-90° C. for 2 h. The reaction mixture was cooled down and 1N HCl solution (10 mL) was added to be acidic. Dichloromethane (100 mL) was then added and the organic phase was further washed with water (100 mL) and dried over sodium sulfate. The solvent was removed and the residue was mixed with ether (50 mL) and stirred for 0.5 h. The solid was filtered and dried to give N-(2-chlorophenyl)-5-(methylsulfonyl)picolinamide 5 as a light yellow solid. Yield: 1.26 g, 87.2%.

Workup

  1. temperatureThe reaction mixture was cooled down
  2. washthe organic phase was further washed with water (100 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed
  5. additionthe residue was mixed with ether (50 mL)
  6. filtrationThe solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-1d2850f5986645d98de8ddc884a7ea13
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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