Acetic Anhydride → 2-n-Tridecyl-5-[2-(1-methyl-5-nitroimidazol-2-yl)-vinyl]-1,3,4-thiadiazole

HRID 1856195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1856195
[CH2:1]([C:14]1[S:15][C:16]([CH3:19])=[N:17][N:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH3:20][N:21]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N:23]=[C:22]1[CH:29]=O.C(OC(=O)C)(=O)C>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH2:1]([C:14]1[S:15][C:16]([CH:19]=[CH:29][C:22]2[N:21]([CH3:20])[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N:23]=2)=[N:17][N:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehydeHCID 233463742-Methyl-5-tridecyl-1,3,4-thiadiazole

Produkt 1

HCID 537391862-n-Tridecyl-5-[2-(1-methyl-5-nitroimidazol-2-yl)-vinyl]-1,3,4-thiadiazoleAusbeute 56,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

8.45 g of 2-tridecyl-5-methyl-1,3,4-thiadiazole, 4.65 g of 1-methyl-5-nitroimidazole-2-carboxaldehyde and 0.5 g of zinc chloride are heated in 40 ml of acetic acid and 15 ml of acetic anhydride for 24 hours at reflux temperature. After the solvent has been removed, the residue is recrystallized from alcohol. 7.1 g of product is obtained, corresponding to 61% of the theory. The melting point is 91° C.

Aufarbeitung

  1. customAfter the solvent has been removed
  2. customthe residue is recrystallized from alcohol

Quellen und Nachweise

ORD-Eintrag
ord-0fb3f5fddbad49e8bda16a28667d452a
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04218460

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