Pyridine → HCID 68676974, compound

HRID 1992203Notes

Reaction equation

HRID 1992203 reaction equation
[NH2:1][C:2]1[C:3]([F:13])=[C:4]([C:9]([F:12])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].N1C=CC=CC=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[F:13][C:3]1[C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:11][CH:10]=[C:9]([F:12])[C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 45480188Methyl 3-amino-2,6-difluorobenzoate

Product 1

HCID 68676974HCID 68676974, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-amino-2,6-difluorobenzoate (530 mg, 2.83 mmol) and pyridine (0.28 mL, 3.40 mmol) in 10 mL CH2Cl2 was added methanesulfonyl chloride (0.24 mL, 3.11 mmol). After 24 h at room temperature, the reaction mixture was washed with saturated aqueous NaHCO3 and extracted with CHCl3 to provide crude methyl 2,6-difluoro-3-[(methylsulfonyl)amino]benzoate as a solid (ESI-MS 264 (M−H)), which was hydrolyzed using aqueous NaOH to provide 2,6-difluoro-3-[(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-6a05b3f058904232abb5da3f02b840ad
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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