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

HRID 1925746Notes

Reaction equation

HRID 1925746 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]3[CH:21]=[CH:20][S:19][C:18]=3[C:22]([O:24]C)=[O:23])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>O1CCCC1.CO>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([S:13]([NH:16][C:17]3[CH:21]=[CH:20][S:19][C:18]=3[C:22]([OH:24])=[O:23])(=[O:15])=[O:14])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59180410Methyl 3-(4-cyclohexylphenylsulfonamido)thiophene-2-carboxylate

Product 1

HCID 251835103-(4-Cyclohexylphenylsulfonamido)thiophene-2-carboxylic acidYield 73.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 128 (0.55 g; 1.46 mmol) in tetrahydrofuran (20 mL) and methanol (7 mL) was added aqueous sodium hydroxide (20 mL; 2N) and then heated at 80° C. for 16 hours. The reaction mixture was allowed to cool to room temperature and then extracted with diethyl ether (20 mL). The aqueous layer was separated and acidified with aqueous hydrochloric acid (15 mL; 2N) then extracted with ethyl acetate (2×20 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield the title product as a gray solid (0.39 g).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether (20 mL)
  3. customThe aqueous layer was separated
  4. extractionthen extracted with ethyl acetate (2×20 mL)
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1bdece020ce40748d1191d732abbbfe
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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