Ethyl ketone → ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-2-(3-methoxypentan-3-yl)-2H-1,2,3-triazole-4-carboxylate

HRID 841971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 841971
O.[C:2]1(C)[CH:7]=[CH:6]C(S(O)(=O)=O)=[CH:4][CH:3]=1.CC[C:15](=[O:18])CC.C(OC)(OC)OC.[CH3:26][O:27][C:28]1[C:45]([O:46][CH3:47])=[CH:44][C:31]([C:32]([C:34]2[NH:38][N:37]=[N:36][C:35]=2[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:33])=[C:30]([N+:48]([O-:50])=[O:49])[CH:29]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:26][O:27][C:28]1[C:45]([O:46][CH3:47])=[CH:44][C:31]([C:32]([C:34]2[C:35]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[N:36][N:37]([C:2]([O:18][CH3:15])([CH2:7][CH3:6])[CH2:3][CH3:4])[N:38]=2)=[O:33])=[C:30]([N+:48]([O-:50])=[O:49])[CH:29]=1

Komponenten

7

Edukt 4

HCID 7288Ethyl ketoneHCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 178470514HCID 178470514, Verbindung

Produkt 1

HCID 22222604ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-2-(3-methoxypentan-3-yl)-2H-1,2,3-triazole-4-carboxylateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

p-Toluenesulfonic acid monohydrate (20 mg) was added to a solution of 3-pentanone (3.1 ml) and trimethyl orthoformate (3.3 ml) in methylene chloride (10 ml). The mixture was heated for one hr with stirring. This solution (4 ml) was added to a solution of ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (Synthesis Example 2) (140 mg) in methylene chloride (2 ml). The mixture was stirred at room temperature for one hr, and triethylamine (0.05 ml) was then added thereto. The mixture was post-treated by a conventional method and subjected to separation and purification to give ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-2-(3-methoxypentan-3-yl)-2H-1,2,3-triazole-4-carboxylate (140 mg, 78%) as a yellow powder.

Aufarbeitung

  1. temperatureThe mixture was heated for one hr
  2. stirringThe mixture was stirred at room temperature for one hr
  3. additionThe mixture was post-treated by a conventional method
  4. customsubjected to separation and purification

Quellen und Nachweise

ORD-Eintrag
ord-a1da1e59376f4493b1f97a6190d14fe6
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372735B1

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