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

HRID 847028Notes

Reaction equation

HRID 847028 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=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.

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-a41b312363da4af998da75fa22510025
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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