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Hydrochloric Acid → 3-(4-Tert-butylphenylsulfonamido)benzo[b]thiophene-2-carboxylic acid

HRID 1925725
Notes
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Reaction equation

HRID 1925725 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:16]3[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=3[S:18][C:19]=2[C:20]([O:22]C)=[O:21])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(#N)C.Cl>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:16]3[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=3[S:18][C:19]=2[C:20]([OH:22])=[O:21])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 59180462Methyl 3-(4-tert-butylphenylsulfonamido)benzo[b]thiophene-2-carboxylate

Product 1

HCID 251833683-(4-Tert-butylphenylsulfonamido)benzo[b]thiophene-2-carboxylic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 88 (0.120 g; 0.31 mmol) in methanol (2 mL) was added aqueous sodium hydroxide (1 mL; 2 mmol; 2N). Acetonitrile (2 mL) was added to aid in solubility, and the resulting mixture was stirred overnight. The reaction mixture was acidified with aqueous hydrochloric acid (2N) and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, decanted, and concentrated under reduced pressure. Trituration of the crude product from hexanes and dichloromethane yielded the desired product as a pink solid (121 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customdecanted
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f937317daac84360b39bd69372390b0e
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178699B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes