1,2-Hydrazinedicarboxaldehyde → methyl 2-methoxy-5-(4H-triazol-1-yl)benzoate

HRID 323450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323450
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[CH:14]([NH:16][NH:17]C=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:34](=O)(O)[O-].[Na+]>CO.ClCCl.C(OCC)(=O)C.ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:34][CH2:14][N:16]=[N:17]2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Komponenten

7

Edukt 4

HCID 123421,2-HydrazinedicarboxaldehydeHCID 14812Phosphorus oxide (P4O10)HCID 89843Methyl 5-amino-o-anisateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 22009369methyl 2-methoxy-5-(4H-triazol-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21226129Dichloromethane methanolLösungsmittelHCID 21226138Dichloromethane ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

Alternately, according to the method of J. Med. Chem., 21, 1100 (1978), combine methyl 2-methoxy-5-aminobenzoate (1.8 g, 10 mmol), diformyl hydrazine (0.97 g, 11 mmol), and phosphorous pentoxide (1.84 g, 13 mmol). Heat to 160° C. After 1.5 hours, cool the reaction mixture and add a saturated aqueous solution of sodium bicarbonate. Extract three times with dichloromethane. Dry the combined organic layers over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 40% ethyl acetate/dichloromethane and then 5% methanol/dichloromethane to give methyl 2-methoxy-5-(4H-triazol-1-yl)benzoate: mp; 179-182° C.

Aufarbeitung

  1. temperaturecool the reaction mixture
  2. extractionExtract three times with dichloromethane
  3. dry with materialDry the combined organic layers over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-51d4e5ada01148b294c4f63a0dbc22fa
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211199B1

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