Isopropanol → Ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-2-(1-isopropoxycarbonyloxy-2-methylpropyl)-2H-1,2,3-triazole-4-carboxylate

HRID 1794694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1794694
[CH3:1][O:2][C:3]1[C:20]([O:21][CH3:22])=[CH:19][C:6]([C:7]([C:9]2[NH:13][N:12]=[N:11][C:10]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:8])=[C:5]([N+:23]([O-:25])=[O:24])[CH:4]=1.[OH2:26].[C:27]1([CH3:37])[CH:32]=CC(S(O)(=O)=O)=C[CH:28]=1.[C:38](N1C=CN=C1)(N1C=CN=C1)=[O:39].[CH:50]([OH:53])([CH3:52])[CH3:51]>C(Cl)Cl>[CH:50]([O:53][C:38]([O:39][CH:32]([N:12]1[N:11]=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([C:7](=[O:8])[C:6]2[CH:19]=[C:20]([O:21][CH3:22])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N+:23]([O-:25])=[O:24])=[N:13]1)[CH:27]([CH3:28])[CH3:37])=[O:26])([CH3:52])[CH3:51]

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 682631,1'-CarbonyldiimidazoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 178470514HCID 178470514, Verbindung

Produkt 1

HCID 22222564Ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-2-(1-isopropoxycarbonyloxy-2-methylpropyl)-2H-1,2,3-triazole-4-carboxylateAusbeute 367 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (Synthesis Example 2) (1.07 g) and p-toluenesulfonic acid monohydrate (53 mg) were suspended in methylene chloride (10 ml) under an argon atmosphere. Isobutyl aldehyde (330 mg) was added to the suspension. The mixture was stirred at room temperature for 25 min. 1,1′-carbonyldiimidazole (744 mg) and methylene chloride (5.0 ml) were added thereto, and the mixture was stirred at room temperature for 25 min. Isopropyl alcohol (920 mg) was added thereto, and the mixture was stirred at room temperature for 3 hr and then refluxed for 21 hr. The mixture was post-treated by a conventional method and subjected to separation and purification to give ethyl 2-(1-isopropoxycarbonyloxy-2-methylpropyl)-5-(4,5-dimethoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate as a light yellow foam (520 mg, 34%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 25 min
  2. stirringthe mixture was stirred at room temperature for 3 hr
  3. temperaturerefluxed for 21 hr
  4. additionThe mixture was post-treated by a conventional method
  5. customsubjected to separation and purification

Quellen und Nachweise

ORD-Eintrag
ord-429318bdb509485392f77b460e3b3a72
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022860B2

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