Acetohydrazide → HCID 22009383, compound

HRID 323456Notes

Reaction equation

HRID 323456 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=S)[CH3:15])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[C:17]([NH:20][NH2:21])(=O)C.[C:22](OCC)(=O)C.ClCCl.CO.ClCCl>C(O)CCC>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH:14]([CH3:15])[CH2:17][N:20]([CH3:22])[NH:21]2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 14039AcetohydrazideHCID 18464819HCID 18464819, compoundHCID 21226129Dichloromethane methanolHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 22009383HCID 22009383, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

According to the method of Heterocycles, 34, 771 (1992), combine methyl 2-methoxy-5-thioacetamidobenzoate (1.00 g, 4.2 mmol) and acetylhydrazine (0.35 g, 4.8 mmol) in n-butanol (8 mL). Heat to reflux. After 18 hours, cool and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 30% ethyl acetate/dichloromethane and then 5% methanol/dichloromethane to give a residue. Recrystallize the residue from ethyl acetate/hexane to give methyl 2-methoxy-5-(3,5-dimethyl-4H-triazol-1-yl)benzoate: mp; 180-182° C.

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. customevaporate in vacuo
  4. customto give a residue
  5. customRecrystallize the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0b2cbcbb0aed4c03b59a0ab187987b74
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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