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

HRID 240278Notes

Reaction equation

HRID 240278 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.[Br: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].[CH3:21]O>OS(O)(=O)=O>[Br: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][CH3:21])=[O:5])=[S:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 1060Pyruvic AcidHCID 86654851N-(2-bromo-5-fluorobenzyl)hydrazinecarbothioamide

Product 1

HCID 86654852Methyl 2-(2-(2-bromo-5-fluorobenzylcarbamothioyl)hydrazono)propanoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of pyruvic acid (352 mg, 4.00 mmol) in methanol (15 mL) was added N-(2-bromo-5-fluorobenzyl)hydrazinecarbothioamide (14, 1.112 g, 4.00 mmol) followed by conc. H2SO4 (5 drops). The mixture was heated at reflux for 7 h. Most of the solvent was evaporated. The residue was taken into EtOAc (150 mL), washed with water, saturated NaHCO3 and brine, dried over MgSO4, and concentrated to give methyl 2-(2-(2-bromo-5-fluorobenzylcarbamothioyl)hydrazono)propanoate (15). MS: m/z, 362 (100%, M+1), 364 (100%), 384 (60%, M+23), 386 (60%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 7 h
  3. customMost of the solvent was evaporated
  4. washwashed with water, saturated NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f3e0d2df598d491fbc3bcb53ae7a4ce3
Source dataset
uspto-grants-2014_02
Patent number
US08648073B2

Reaction notes

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