methyl 5-(N-(4-(dimethylcarbamoyl)phenyl)-sulfamoyl)-thiophene-2-carboxylate → 5-(N-(4-(dimethylcarbamoyl)phenyl)sulfamoyl)thiophene-2-carboxylic acid

HRID 59759Notes

Reaction equation

HRID 59759 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([C:15]2[S:19][C:18]([C:20]([O:22]C)=[O:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:7][CH:6]=1)=[O:4]>CO.[OH-].[Na+]>[CH3:1][N:2]([CH3:24])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([C:15]2[S:19][C:18]([C:20]([OH:22])=[O:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 86703866methyl 5-(N-(4-(dimethylcarbamoyl)phenyl)-sulfamoyl)-thiophene-2-carboxylate

Product 1

HCID 867038655-(N-(4-(dimethylcarbamoyl)phenyl)sulfamoyl)thiophene-2-carboxylic acidYield 56.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of methyl 5-(N-(4-(dimethylcarbamoyl)phenyl)-sulfamoyl)-thiophene-2-carboxylate (Int. 75) (100 mg, 0.271 mmol) in methanol (10 ml), sodium hydroxide 1M (1 ml) was added, and the mixture stirred at RT for 4 days with monitoring the progress of reaction and adding further amounts of NaOH 1M until completion. MeOH was evaporated under reduced pressure and the crude taken up with HCl 1N and AcOEt. The organic phase was dried over Na2SO4 and concentrated under vacuum to give 54 mg of 5-(N-(4-(dimethylcarbamoyl)phenyl)sulfamoyl)thiophene-2-carboxylic acid (Int. 76).

Workup

  1. customthe progress of reaction
  2. customMeOH was evaporated under reduced pressure
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-56e5d69ee0334d17b8e523a2c99c1a4d
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

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