Pyridine → HCID 54300325, compound

HRID 2378362Notes

Reaction equation

HRID 2378362 reaction equation
C[NH:2][C:3]1[C:4](=[CH:8][C:9]([CH3:13])=[CH:10][C:11]=1[CH3:12])[C:5]([OH:7])=[O:6].[F:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.N1C=CC=C[CH:26]=1>C(Cl)(Cl)Cl>[CH3:26][O:7][C:5](=[O:6])[C:4]1[CH:8]=[C:9]([CH3:13])[CH:10]=[C:11]([CH3:12])[C:3]=1[NH:2][S:21]([C:18]1[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 69308774HCID 69308774, compound

Product 1

HCID 54300325HCID 54300325, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.00 g (0.011 mmol) of methyl 3,5-dimethylanthranilic acid in 10.0 mL of pyridine was added 2.17 (0.011 mmol) of 4-fluorobenzenesulfonyl chloride. The reaction mixture was stirred for 24 h at room temperature and then diluted with chloroform and washed with 5% HCl solution and water. The organic layer was then dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether-hexanes and the resulting solid was filtered and dried to provide 3.09 g (82%) of the desired product as a white solid. Electrospray Mass Spec: m/z 338.3 (M+H)+.

Workup

  1. washwashed with 5% HCl solution and water
  2. dry with materialThe organic layer was then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ether-hexanes
  6. filtrationthe resulting solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-e2286824226b4dacb0cd537a8bc39b70
Source dataset
uspto-grants-2008_12
Patent number
US07470794B2

Reaction notes

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