Pyridine → HCID 60726642, compound

HRID 1992202Notes

Reaction equation

HRID 1992202 reaction equation
[NH2:1][C:2]1[C:3]([F: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>[F:12][C:5]1[CH:4]=[C:3]([F:13])[C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 22110105Methyl 5-amino-2,4-difluorobenzoate

Product 1

HCID 60726642HCID 60726642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-amino-2,4-difluorobenzoate (252 mg, 1.35 mmol) and pyridine (0.13 mL, 1.61 mmol) in 5 mL CH2Cl2 was added methanesulfonyl chloride (0.12 mL, 1.48 mmol). After 24 h at room temperature, the reaction mixture was washed with saturated aqueous NaHCO3 and extracted with CHCl3 to provide crude methyl 2,4-difluoro-5-[(methylsulfonyl)amino]benzoate as a solid (ESI-MS 264 (M−H)), which was hydrolyzed using aqueous NaOH to provide 2,4-difluoro-5-[(methylsulfonyl)amino]benzoic acid (ESI-MS 250 (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-a7117e1b38b84bb0b0d5a31482239022
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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