Thiophene-2-carbohydrazide → 2-[3-sulfanyl-5-(thiophen-2-yl)-4H-1,2,4-triazol-4-yl]acetic acid

HRID 2102286

Reaction equation

HRID 2102286 reaction equation
[S:1]=[C:2]=[N:3][CH2:4][C:5]([O:7]C)=[O:6].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([NH:16][NH2:17])=O>C(O)(C)C>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]1[N:3]([CH2:4][C:5]([OH:7])=[O:6])[C:2](=[S:1])[NH:17][N:16]=1

Participants

4

Reactant 2

HCID 73098Thiophene-2-carbohydrazideHCID 140795Methyl 2-isothiocyanatoacetate

Product 1

HCID 49625532-[3-sulfanyl-5-(thiophen-2-yl)-4H-1,2,4-triazol-4-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Methyl N-(thioxomethylene)glycinate (2.06 g) and thiophene-2-carbohydrazide (2.57 g) in isopropanol (50 ml) was heated at 70° C. while stirring for 16 h. The mixture was allowed to come to r.t. and the formed precipitate collected and heated at reflux in 1.0 M aqueous NaHCO3 solution for 2 h. After cooling to r.t. and acidification with conc. HCl (aq.) the product was extracted into EA, which was washed with brine and then dried over MgSO4 before concentration to dryness to yield crude title compound which was used directly in the next step.

Workup

  1. customto come to r.t.
  2. customthe formed precipitate collected
  3. temperatureheated
  4. temperatureat reflux in 1.0 M aqueous NaHCO3 solution for 2 h
  5. extractionacidification with conc. HCl (aq.) the product was extracted into EA, which
  6. washwas washed with brine
  7. dry with materialdried over MgSO4 before concentration to dryness

Sources & evidence

ORD record
ord-4cb66b5c39fd4368b8e29fbcc8210ca3
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Linked notes

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