Sodium Hydroxide → 3-(4-Tert-butylbenzenesulfonamido)thiophene-2-carboxylic acid

HRID 1925708

Reaction equation

HRID 1925708 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([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:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([OH:22])=[O:21])(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 8015643Methyl 3-(4-tert-butylphenylsulfonamido)thiophene-2-carboxylate

Product 1

HCID 446106033-(4-Tert-butylbenzenesulfonamido)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 55 (0.817 g; 2.31 mmol) in methanol (4.5 mL) was added aqueous sodium hydroxide (9.2 mL; 1N). After the reaction was complete, the mixture was partitioned between diethyl ether and water; the organic layer was separated and set aside. The aqueous layer was acidified with excess aqueous hydrochloric acid (2N) and extracted with ethyl acetate (2×). The diethyl ether and ethyl acetate organic layers were combined, dried over sodium sulfate, decanted, and concentrated under reduced pressure. The resulting residue yielded the desired product a white solid from a mixture of hexanes and dichloromethane (0.54 g).

Workup

  1. customthe mixture was partitioned between diethyl ether and water
  2. customthe organic layer was separated
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialdried over sodium sulfate
  5. customdecanted
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7fc01462c944078a78037d3c50f0125
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Linked notes

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