2-Methoxyacetohydrazide → methyl 2-isopropyl-5-(5-(methoxymethyl)-4H-1,2,4-triazol-3-yl)-4-methylbenzoate

HRID 541315Notes

Reaction equation

HRID 541315 reaction equation
[NH:1]=[C:2](SC)[C:3]1[C:4]([CH3:16])=[CH:5][C:6]([CH:13]([CH3:15])[CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].[CH3:19][O:20][CH2:21][C:22]([NH:24][NH2:25])=O>C(O)(=O)C>[CH:13]([C:6]1[CH:5]=[C:4]([CH3:16])[C:3]([C:2]2[NH:1][C:22]([CH2:21][O:20][CH3:19])=[N:24][N:25]=2)=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 27595322-Methoxyacetohydrazide2×HCID 68288919Methyl 5-(imino(methylthio)methyl)-2-isopropyl-4-methylbenzoate2×

Product 1

HCID 178494710methyl 2-isopropyl-5-(5-(methoxymethyl)-4H-1,2,4-triazol-3-yl)-4-methylbenzoateYield 27.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of methyl 5-(imino(methylthio)methyl)-2-isopropyl-4-methylbenzoate (compound 196.5, 800 mg, 3.01 mmol, 1.00 equiv) and 2-methoxyacetohydrazide (compound 190.6, 1.90 g, 18.3 mmol, 5.00 equiv) in acetic acid (30 mL) was stirred for 2 h at 80° C. in an oil bath, then concentrated in vacuo. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:50-1:2) as eluent to yield 250 mg (27%) of methyl 2-isopropyl-5-(5-(methoxymethyl)-4H-1,2,4-triazol-3-yl)-4-methylbenzoate as a clear oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified

Sources & evidence

ORD record
ord-7b5c7239c3c9404ebcb58f8f9ed19390
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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