Hydrochloric Acid → 3-(4-sec-Butylphenylsulfonamido)thiophene-2-carboxylic acid

HRID 1925703Notes

Reaction equation

HRID 1925703 reaction equation
[CH: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)([CH2:3][CH3:4])[CH3:2].[OH-].[Na+].Cl>O1CCCC1>[CH: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)([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19683026Methyl 3-[4-(sec-butyl)phenylsulfonamido]thiophene-2-carboxylate

Product 1

HCID 251838013-(4-sec-Butylphenylsulfonamido)thiophene-2-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 52 (0.75 g, 2.12 mmol) in tetrahydrofuran (10 mL) was added aqueous sodium hydroxide (5 mL, 2N). The reaction mixture was heated at 65° C. for 2 days, allowed to cool to room temperature and then acidified to pH 5 with aqueous hydrochloric acid (2N) and extracted with tetrahydrofuran (3×5 mL). The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield a golden oil (0.7 g), which later solidified. A portion of the crude residue was purified by preparative HPLC to afford the title compound as a white solid (129 mg).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with tetrahydrofuran (3×5 mL)
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ee1e60a2412435e8d77363b5ee5a531
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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