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

HRID 1943968Notes

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 the mixture was 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
extractionthe mixture was extracted with EtOAc (3×6 mL)

Sources & evidence

ORD record: ord-6f2b4d36250241eaaccb28e12c8f1eb3
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394795B2

Reaction notes

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