Methanol → Methyl 4-(3-oxo-2,3-dihydro-1,2,4-triazin-6-yl)benzoate

HRID 2245974Notes

Reaction equation

HRID 2245974 reaction equation
C(O[CH:4](OCC)[C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)=O)C.Cl.[NH2:21][NH:22][C:23]([NH2:25])=[O:24].C(N(CC)C(C)C)(C)C.CO>ClCCCl.C(Cl)Cl>[O:24]=[C:23]1[N:25]=[CH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=2)=[N:21][NH:22]1

Participants

7

Reactant 4

HCID 887MethanolHCID 11236Semicarbazide hydrochloride2×HCID 81531DiisopropylethylamineHCID 59216300Methyl 4-(diethoxyacetyl)benzoate

Product 1

HCID 59216301Methyl 4-(3-oxo-2,3-dihydro-1,2,4-triazin-6-yl)benzoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of methyl 4-(diethoxyacetyl)benzoate (15.4 g, 0.0578 mol), semicarbazide hydrochloride (7.1 g, 0.064 mol), N,N-diisopropylethylamine (12 mL, 0.069 mol) in 1,2-dichloroethane (150 mL), and methanol (2 mL) was heated at 95° C. for 4 h. To the mixture was added an additional 0.1 equivalents of semicarbazide hydrochloride. The mixture was stirred at 95° C. for 1 h. After cooling, the mixture was diluted with methylene chloride and washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was refluxed with acetic acid (100 mL) and water (1.0 mL) overnight. The mixture was concentrated to yield quantitative crude material which was directly used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperatureThe residue was refluxed with acetic acid (100 mL) and water (1.0 mL) overnight
  7. concentrationThe mixture was concentrated
  8. customto yield quantitative crude material which
  9. customwas directly used in the next step without further purification

Sources & evidence

ORD record
ord-c091933d3ccc417681f0293506058408
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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