Methanol → Methyl 2-(2-(2-chloro-5-fluorobenzylcarbamothioyl)hydrazono)propanoate

HRID 240290Notes

Reaction equation

HRID 240290 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.[Cl:7][C:8]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:9]=1[CH2:10][NH:11][C:12]([NH:14][NH2:15])=[S:13].OS(O)(=O)=O.[CH3:26]O>>[Cl:7][C:8]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:9]=1[CH2:10][NH:11][C:12]([NH:14][N:15]=[C:2]([CH3:4])[C:1]([O:6][CH3:26])=[O:5])=[S:13]

Participants

5

Reactant 4

HCID 887MethanolHCID 1060Pyruvic AcidHCID 1118Sulfuric AcidHCID 86654854N-(2-chloro-5-fluorobenzyl)hydrazinecarbothioamide

Product 1

HCID 86654855Methyl 2-(2-(2-chloro-5-fluorobenzylcarbamothioyl)hydrazono)propanoate

Procedure

To a solution of pyruvic acid (5.63 g, 64.0 mmol) in methanol (150 mL) was added N-(2-chloro-5-fluorobenzyl)hydrazinecarbothioamide (27, 14.9 g, 64.0 mmol) followed by cone. H2SO4 (3 mL) The mixture was heated at reflux for 15 h. Most of the solvent was evaporated. The resulting residue was taken into EtOAc (500 mL), washed with water, saturated NaHCO3 and brine, dried over MgSO4, and concentrated to give methyl 2-(2-(2-chloro-5-fluorobenzylcarbamothioyl)hydrazono)propanoate (28). MS: m/z, 318 (100%, M+1), 320 (35%).

Workup

  1. temperatureat reflux for 15 h
  2. customMost of the solvent was evaporated
  3. washwashed with water, saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6d15ae8f2bcb41f5b90797129474125f
Source dataset
uspto-grants-2014_02
Patent number
US08648073B2

Reaction notes

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