Hydrochloric Acid → 2-(2-Dodecyl-2H-tetrazol-5-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

HRID 264046

Reaktionsgleichung

Reaktionsgleichung von HRID 264046
[CH2:1]([N:13]1[N:17]=[N:16][C:15]([CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([OH:21])=O)=[N:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:40][O:41][C:42]1[CH:48]=[C:47]([O:49][CH3:50])[CH:46]=[C:45]([O:51][CH3:52])[C:43]=1[NH2:44].Cl>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:13]1[N:17]=[N:16][C:15]([CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([NH:44][C:43]2[C:45]([O:51][CH3:52])=[CH:46][C:47]([O:49][CH3:50])=[CH:48][C:42]=2[O:41][CH3:40])=[O:21])=[N:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 842712,4,6-TrimethoxyanilineHCID 10523337alpha-(2-Dodecyl-2H-5-tetrazolyl)phenylacetic acid

Produkt 1

HCID 98934132-(2-Dodecyl-2H-tetrazol-5-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The compound obtained in (d) above (6.58 g; 17.6 mmoles) was dissolved in tetrahydrofuran (50 mL), treated with carbonyldiimidazole (3.1 g; 19.1 mmoles), and stirred for 1 hour at room temperature under an atmosphere of N2. A solution of 2,4,6-trimethoxyaniline (3.2 g; 17.6 mmoles/50 mL THF) was then added in one portion and the solution was stirred at room temperature for overnight. Ethyl acetate (150 mL) was then added as well as aqueous HCl (1N). The layers were separated and the organic portion was washed with NaOH (1N), brine, and then dried over MgSO4. The drying agent was filtered and the filtrate concentrated in vacuo leaving a lavender colored solid which was purified by silica gel chromatography using chloroform (95%)/methanol (5%) as the eluent. Yield: 6.7 g (70%), mp 119°-120° C.

Aufarbeitung

  1. stirringthe solution was stirred at room temperature for overnight
  2. customThe layers were separated
  3. washthe organic portion was washed with NaOH (1N), brine
  4. dry with materialdried over MgSO4
  5. filtrationThe drying agent was filtered
  6. concentrationthe filtrate concentrated in vacuo
  7. customleaving a lavender colored solid which
  8. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cef04950952e48a2aa73a44402945d2a
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646170

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