Sodium Hydroxide → HCID 66717650, compound

HRID 1182260Notes

Reaction equation

HRID 1182260 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](=[O:22])(=[O:21])[N:11]([CH2:18][O:19][CH3:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].[OH-].[Na+]>CO.O>[CH3:20][O:19][CH2:18][N:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[S:10]([C:9]1[CH:8]=[CH:7][S:6][C:5]=1[C:3]([OH:4])=[O:2])(=[O:22])=[O:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66717624HCID 66717624, compound

Product 1

HCID 66717650HCID 66717650, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a homogenous mixture of 3-(N-methoxymethyl-N-phenylsulfamoyl)thiophene-2-carboxylic acid methyl ester (3 g, 8.75 mmol) in methanol and water was added aqueous, sodium hydroxide solution (2N, excess) at room temperature. Upon completion of the reaction, the mixture was cooled and extracted once with diethyl ether. The aqueous layer will then acidified with aqueous, HCl (2N, excess) before re-extracting twice with ethyl acetate. The organic layer was washed once with brine solution and dried over anhydrous sodium sulfate. The ethyl acetate solution was decanted and evaporated under reduced pressure to give the desired 3-(N-methoxymethyl-N-phenylsulfamoyl)thiophene-2-carboxylic acid (2.2 g, 79%).

Workup

  1. additionwas added aqueous
  2. customat room temperature
  3. customUpon completion of the reaction
  4. temperaturethe mixture was cooled
  5. extractionextracted once with diethyl ether
  6. extractionbefore re-extracting twice with ethyl acetate
  7. washThe organic layer was washed once with brine solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe ethyl acetate solution was decanted
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-66535b3da84c4ed7858241a187955352
Source dataset
uspto-grants-2007_10
Patent number
US07288538B2

Reaction notes

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