Pyridine → HCID 68675765, compound

HRID 1992204Notes

Reaction equation

HRID 1992204 reaction equation
[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].N1C=CC=CC=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[Cl:13][C:3]1[C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:12])[CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 63022791Methyl 5-amino-4-chloro-2-fluorobenzoate

Product 1

HCID 68675765HCID 68675765, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-amino-4-chloro-2-fluorobenzoate (248 mg, 1.22 mmol) and pyridine (0.12 mL, 1.46 mmol) in 5 mL CH2Cl2 was added methanesulfonyl chloride (0.10 mL, 1.34 mmol). After 5 days at room temperature, the reaction mixture was washed with saturated aqueous NaHCO3 and extracted with CHCl3 to provide crude methyl 4-chloro-2-fluoro-5-[(methylsulfonyl)amino]benzoate as a solid (ESI-MS 280 (M−H)), which was hydrolyzed using aqueous NaOH to provide 4-chloro-2-fluoro-5-[(methylsulfonyl)amino]benzoic acid (ESI-MS 266 (M−H)), which was used without further purification.

Workup

  1. washthe reaction mixture was washed with saturated aqueous NaHCO3
  2. extractionextracted with CHCl3

Sources & evidence

ORD record
ord-0706a7f48037456e9ab4162badc35770
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

Loading…