Sodium Hydroxide → 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoic acid

HRID 2196740Notes

Reaction equation

[OH-].[Na+].[CH2:3]([N:5]([C:11]1[C:12]([F:22])=[C:13]([C:18]([F:21])=[CH:19][CH:20]=1)[C:14]([O:16]C)=[O:15])[S:6](=[O:10])(=[O:9])[NH:7][CH3:8])[CH3:4]>C1COCC1.CO>[CH2:3]([N:5]([C:11]1[C:12]([F:22])=[C:13]([C:18]([F:21])=[CH:19][CH:20]=1)[C:14]([OH:16])=[O:15])[S:6](=[O:9])(=[O:10])[NH:7][CH3:8])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

NaOH (0.908 mL, 1.82 mmol) was added to methyl 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoate (0.280 g, 0.908 mmol) in THF-MeOH (3:2; 5 mL). The mixture was warmed to 60° C. for 16 hours. The cooled mixture was concentrated under reduced pressure, and the residue was taken up in 1M NaOH (4 mL) and washed with EtOAc. The aqueous pH was lowered to below 3 and extracted with EtOAc (3×6 mL) to provide crude 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoic acid (222 mg, 83% yield).

Workup

concentrationThe cooled mixture was concentrated under reduced pressure
washwashed with EtOAc
extractionextracted with EtOAc (3×6 mL)

Sources & evidence

ORD record: ord-550d36c9c4944d419e3698b0a9193050
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

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