Triethylamine → 3-Rhodanineacetic acid, ethyl ester

HRID 446056

Reaction equation

HRID 446056 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[C:9](=S)([S:15]CC(O)=O)[S:10][CH2:11][C:12](O)=[O:13].C(N(CC)CC)C>CC(O)C>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][N:7]1[C:12](=[O:13])[CH2:11][S:10][C:9]1=[S:15])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 806183,5-Dithia-4-thioxo-1,7-heptanedioic acidHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 1410093-Rhodanineacetic acid, ethyl esterYield 80.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Separately, glycine ethyl ester hydrochloride (140 mg, 1 mmol) and bis(carboxymethyl) trithiocarbonate (224 mg, 1 mmol) were dissolved in 2-propanol (6 mL), triethylamine (0.6 mL) was added thereto, and the mixture was heated to reflux for 1 hour while stirring. After the reaction was completed the solvent was removed by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (1/1 (volume ratio)) as an eluent, to give ethyl-2-(4-oxo-2-thioxothiazolidin-3-yl)acetate in a yield of 177 mg (yield 80.8%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customwas removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-924fc1cf14a747a3a1379347c1e9ac82
Source dataset
uspto-grants-2013_07
Patent number
US08476449B2

Linked notes

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