Hydrochloric Acid → 3-Methanesulfonamidothiophene-2-carboxylic acid

HRID 59736Notes

Reaction equation

HRID 59736 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([O:13]C)=[O:12])(=[O:4])=[O:3].[OH-].[Na+].Cl>C1COCC1>[CH3:1][S:2]([NH:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([OH:13])=[O:12])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2820039Methyl 3-[(methylsulfonyl)amino]-2-thiophenecarboxylate

Product 1

HCID 167739453-Methanesulfonamidothiophene-2-carboxylic acidYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 3-(methylsulfonamido)thiophene-2-carboxylate (Int. 37) (193 mg, 0.820 mmol) in aqueous 2M NaOH (4.10 ml, 8.20 mmol) and THF (4.1 ml) was heated under microwaves irradiation at 80° C. for 30 minutes. 2N HCl was added (pH=2) and the mixture was extracted with EtOAc (×3). The combined organic layers were dried over Na2SO4 and evaporated to dryness affording 3-(methylsulfonamido)thiophene-2-carboxylic acid (Int. 38) (180 mg, 0.814 mmol, MS/ESI+221.8 [MH]+).

Workup

  1. extractionthe mixture was extracted with EtOAc (×3)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-8d21414f44dc44008c1ab88ce760d784
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

Loading…