Formaldehyde → HCID 12011184, compound

HRID 1635574Notes

Reaction equation

HRID 1635574 reaction equation
[CH2:1]=[O:2].[Cl:3][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][N:7]1[C:11]([CH3:12])=[C:10]([CH3:13])[N:9]=[CH:8]1>C(O)(=O)C>[Cl:3][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][N:7]1[C:11]([CH3:12])=[C:10]([CH3:13])[N:9]=[C:8]1[CH2:1][OH:2]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 120111831-[(2-Chlorophenyl)methyl]-4,5-dimethyl-1H-imidazole

Product 1

HCID 12011184HCID 12011184, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
127.5 °C

Procedure

To a solution of 10 ml of glacial acetic acid and 10 ml of 37% formaldehyde is added 2.67 g (0.012 mol) of 1-(2′-chlorobenzyl)-4,5-dimethylimidazole. The mixture is stirred and heated in a sealed tube at 125-130° C. (oil bath temperature) overnight. After cooling, the solvent is evaporated in vacuo. The residue is subjected to chromatography on silica gel using dichloromethane-methanol (10:1) as eluent to give 2.39 g (79%) of 1-(2′-chlorobenzyl)-4,5-dimethyl-2-hydroxymethylimidazole as colorless powder. MS m/z (M++1) 251; 1H-NMR 400 MHz(δ, CDCl3): 1.94 (3H, s), 2.11 (3H, s), 4.53 (2H, s), 5.26 (2H, s), 6.42 (1H, dd, J=8, 1.2 Hz), 7.14(1H, td, J=8, 1.2Hz), 7.21 (1H, td, J=7.4, 1.6 Hz), 7.39 (1H, dd, J=8, 1.2 Hz) ppm.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-e26978646e6a4a2e8b79a0043b85b9ae
Source dataset
uspto-grants-2003_01
Patent number
US06509366B2

Reaction notes

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