Sodium → 4-(2-chloro-5-fluorobenzyl)-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one

HRID 524124

Reaction equation

HRID 524124 reaction equation
CO[Na].[Na].[Cl:5][C:6]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:7]=1[CH2:8][NH:9][C:10]([NH:12][N:13]=[C:14]([CH3:19])[C:15](OC)=[O:16])=[S:11]>CO>[Cl:5][C:6]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:7]=1[CH2:8][N:9]1[C:15](=[O:16])[C:14]([CH3:19])=[N:13][NH:12][C:10]1=[S:11]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 86654855Methyl 2-(2-(2-chloro-5-fluorobenzylcarbamothioyl)hydrazono)propanoateHCID 178418582HCID 178418582, compound

Product 1

HCID 583285444-(2-chloro-5-fluorobenzyl)-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of MeONa (0.82 M) in methanol (200 mL), freshly prepared from sodium (3.80 g, 165 mmol) and dry methanol (200 mL), was added methyl 2-(2-(2-chloro-5-fluorobenzylcarbamothioyl)hydrazono)propanoate (28, 10.00 g, 31.5 mmol). The mixture was heated at reflux for 36 h. Most of the solvent was evaporated. The resulting residue was diluted with water (300 mL), acidified with 2 N HCl to pH=1˜2, and then extracted with EtOAc (250 mL×2). The extracts were washed with brine, dried over MgSO4, and concentrated to give a mixture, which was separated by silica gel column, and eluted with 20-30% ethyl acetate in petroleum ether to give 4-(2-chloro-5-fluorobenzyl)-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one (29).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 36 h
  3. customMost of the solvent was evaporated
  4. additionThe resulting residue was diluted with water (300 mL)
  5. extractionextracted with EtOAc (250 mL×2)
  6. washThe extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customto give a mixture, which
  10. customwas separated by silica gel column
  11. washeluted with 20-30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-8866f6d245504509a6c825891bece40b
Source dataset
uspto-grants-2016_05
Patent number
US09340523B2

Linked notes

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