1-(4-Nitrobenzyl)-2-butyl-4-chloro-5-hydroxymethyl imidazole → 2-Butyl-5-chloro-3-(4-nitro-benzyl)-3h-imidazole-4-carbaldehyde

HRID 466444Notes

Reaction equation

HRID 466444 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][N:9]2[C:13]([CH2:14][OH:15])=[C:12]([Cl:16])[N:11]=[C:10]2[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]>C(Cl)Cl.O=[Mn]=O>[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][N:9]2[C:13]([CH:14]=[O:15])=[C:12]([Cl:16])[N:11]=[C:10]2[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 153564431-(4-Nitrobenzyl)-2-butyl-4-chloro-5-hydroxymethyl imidazole

Product 1

HCID 198153972-Butyl-5-chloro-3-(4-nitro-benzyl)-3h-imidazole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1 g of 1-(4-nitrobenzyl)-2-butyl-4-chloro-5-hydroxymethyl imidazole and 5 g of activated MnO2 in CH2Cl2 was stirred at room temperature for 16 hours. The reaction mixture was filtered through celite and the filtrate was concentrated to give a thick oil which was purified by flash column chromatography on silica gel (Hexane:ethyl acetate=1.5:1 elution). The desired compound was obtained as a colorless solid, 0.76 g; m.p. 88°-89°; NMR (200 MHz, CDCl3): δ 9.74 (2, 1 h); 5.64 (s, 2H); 2.63 (t, 3H, J=7.4 Hz); 1.68 (m, 2H); 1.34 (m, 2H); 0.89 (t, 3H, J=7.3 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customto give a thick oil which
  4. customwas purified by flash column chromatography on silica gel (Hexane:ethyl acetate=1.5:1 elution)

Sources & evidence

ORD record
ord-1528994b7e624e43a8bb9144b5fe7bf9
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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