Reaction #2467985

ord-9d75b84e991d4bfeb9143586b11b1cb4

Reaction equation

COC(=O)c1cscc1N.Cl
Methyl 4-aminothiophene-3-carboxylate hydrochloride
N
ammonia
COC(=O)c1cscc1N
oil
Yield 65.0%
COC(=O)c1cscc1N
Methyl 4-aminothiophene-3-carboxylate
Yield 65.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ExtractionThe solution was extracted with chloroform
  2. 2
    Washthe combined chloroform layer was washed with water, brine
  3. 3
    Dryingdried over sodium sulfate
  4. 4
    FiltrationThe solution was filtered
  5. 5
    Otherevaporated the solvent

Procedure

Methyl 4-aminothiophene-3-carboxylate hydrochloride (290 mg) was dissolved in water (20 mL) and basified with ammonia solution. The solution was extracted with chloroform and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the product as pale yellow color oil (150 mg, 65%). 1H NMR (400 MHz, CDCl3): δ 7.92 (1H, d, J=3.6 Hz), 6.08 (1H, d, J=3.6 Hz), 4.79 (2H, br s), 3.85 (3H, s).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08258119B2uspto-grants-2012_09