Methanol → 2-n-Butyl-4-chloro-5-methoxymethyl-1-(4-nitrobenzyl)imidazole

HRID 465774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465774
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.[CH3:28]O>>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)[C:7]([CH2:11][O:12][CH3:28])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 153564431-(4-Nitrobenzyl)-2-butyl-4-chloro-5-hydroxymethyl imidazole

Produkt 1

HCID 537649382-n-Butyl-4-chloro-5-methoxymethyl-1-(4-nitrobenzyl)imidazole

Versuchsvorschrift

2-n-butyl-4-chloro-5-hydroxymethyl-1-(4-nitrobenzyl)imidazole (10.5 g, 32.4 mmol, 1 eq), conc. sulfuric acid (26 mL) and methanol (300 mL) were mixed and refluxed overnight. The solvent was removed in vacuo and the residue taken up in water (about 300 mL). The pH was adjusted to 5 with 1N NaOH and then this aqueous portion extracted with ethyl acetate (3× 250 mL). The organic layers were collected, dried (MgSO4) and the solvent removed in vacuo to yield 11.57 g of an amber oil. NMR (200 MHz, CDCl3) δ8.22 (d, 2H, J=8 Hz); 7.15 (d, 2H, J=8 Hz); 5.26 (s, 2H); 4.25 (s, 2H); 3.23 (s, 3H); 2.52 (t, 2H, J=7 Hz); 1.64 (t of t, 2H, J=7,7 Hz); 1.28 (t of q, 2H, J=7,7 Hz); 0.81 (t, 3H, J=7 Hz). Anal. Calcd. for C16H20ClN3O3.(H2O)0.5 : C, 55.41; H, 6.10; Cl, 10.22. Found: C, 55.21; H, 6.22; Cl, 9.92.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. customThe solvent was removed in vacuo
  3. extractionthis aqueous portion extracted with ethyl acetate (3× 250 mL)
  4. customThe organic layers were collected
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-79cfbc3dee044deba9343d14afe98572
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153197

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