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

HRID 653867Notes

Reaction equation

HRID 653867 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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) δ 8.22 (d, 2H, J=8Hz); 7.15 (d, 2H, J=8Hz); 5.26 (s, 2H); 4.25 (s, 2H); 3.23 (s, 3H); 2.52 (t, 2H, J=7Hz); 1.64 (t of t, 2H, J=7,7Hz); 1.28 (t of q, 2H, J=7,7Hz); 0.81 (t, 3H, J=7Hz). 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.

Workup

  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

Sources & evidence

ORD record
ord-6e6885d9ec0241c8815bf7c60c70c467
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

Loading…