Hydrochloric Acid → 3-[[2-(4-Methoxyphenyl)acetyl]amino]-2-thiophenecarboxylic acid

HRID 2097969Notes

Reaction equation

HRID 2097969 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[CH:17]=[CH:16][S:15][C:14]=2[C:18]([O:20]C)=[O:19])=[O:11])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[CH:17]=[CH:16][S:15][C:14]=2[C:18]([OH:20])=[O:19])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 897877HCID 897877, compound

Product 1

HCID 201196553-[[2-(4-Methoxyphenyl)acetyl]amino]-2-thiophenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

Methyl 3-(2-(4-methoxyphenyl)acetamido)thiophene-2-carboxylate (5.7 g, 18.7 mmol) was dissolved in THF/H2O (40 mL, 4/1, v/v). Sodium hydroxide (2.24 g, 56.1 mmol) was added and the reaction mixture was stirred at 60° C. for 8 h. The resulting solution was acidified with 10% aqueous HCl and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), filtered and concentrated under vacuum to give 3-(2-(4-methoxyphenyl)acetamido)thiophene-2-carboxylic acid. Retention time (min)=1.678, method [1], MS (ESI) 292.1 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-95d79d862e144773aa3a856cf56337d0
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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