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

HRID 2196740
Notes
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Reaction equation

HRID 2196740 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67052525methyl 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoate

Product 1

HCID 670525023-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoic acidYield 83.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

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

  1. concentrationThe cooled mixture was concentrated under reduced pressure
  2. washwashed with EtOAc
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes