Methanol → 3-(3-(Dimethylcarbamoyl)phenylsulfonamido)thiophene-2-carboxylic acid

HRID 59762Notes

Reaction equation

HRID 59762 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]([C:5]1[CH:6]=[C:7]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([O:22]C)=[O:21])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)=[O:4].CO.[OH-].[Na+]>Cl>[CH3:1][N:2]([CH3:24])[C:3]([C:5]1[CH:6]=[C:7]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([OH:22])=[O:21])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86703867Methyl 3-(3-(dimethylcarbamoyl)phenylsulfonamido)thiophene-2-carboxylate

Product 1

HCID 867038683-(3-(Dimethylcarbamoyl)phenylsulfonamido)thiophene-2-carboxylic acidYield 77.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methyl 3-(3-(dimethylcarbamoyl)phenylsulfonamido)thiophene-2-carboxylate (Int. 79, 200 mg, 0.543 mmol) was dissolved in MeOH (4 ml, 99 mmol). NaOH 1M (2 ml) was added, and the reaction was stirred at RT for 8 hours to achieve completion. The reaction mixture was diluted with HCl 1N and extracted with AcOEt. The organic phase was washed with HCl 1N and brine, dried over Na2SO4 and concentrated under vacuum to give 3-(3-(dimethylcarbamoyl)phenylsulfonamido)thiophene-2-carboxylic acid (Int. 80, 150 mg, 0.423 mmol).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic phase was washed with HCl 1N and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-39255a2744ef4cf0bfbe7f6bc92d570b
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

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