Formaldehyde → Methyl 4-[[2-ethyl-4-methyl-1H-imidazol-1-yl]methyl]benzoate

HRID 274600Notes

Reaction equation

HRID 274600 reaction equation
[CH2:1]([C:3]1[NH:4][CH:5]=[C:6]([CH3:8])[N:7]=1)[CH3:2].[C:9]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1)([O:11][CH3:12])=[O:10].N1C=CN=C1.CC([O-])=O.[Na+].C=O>CC(O)=O>[CH2:1]([C:3]1[N:4]([CH2:17][C:16]2[CH:19]=[CH:20][C:13]([C:9]([O:11][CH3:12])=[O:10])=[CH:14][CH:15]=2)[CH:5]=[C:6]([CH3:8])[N:7]=1)[CH3:2]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 795ImidazoleHCID 256687Methyl 4-(bromomethyl)benzoateHCID 517045Sodium AcetateHCID 178437635HCID 178437635, compound

Product 1

HCID 20093489Methyl 4-[[2-ethyl-4-methyl-1H-imidazol-1-yl]methyl]benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl 4-[[2-ethyl-4-methyl-1H-imidazol-1-yl]methyl]benzoate compound was prepared from 2-ethyl-4-methyl-imidazole and (4-carbmethoxy) benzylbromide in an analogous fashion as described in Example 11. A solution of the above imidazole (2.17 g, 8.14 mmol), NaOAc (1.17 g), 37 % HCHO (10 mn) , and AcOH (1.2 mn) was heated under reflux for 22 hours. The solution was evaporated under vacuo, and the residue was stirred with 10 mL of 20% NaOH solution for 2 hours. It was diluted with water and the solution was extracted with CH2Cl2. The extract was washed with water, dried, and evaporated to an oil. It was chromatographed (CH2Cl2 /MeOH, 2-5%) to give 1.0 g of the desired hydroxymethyl compound as a foam. MS (CI 288 (m).

Workup

  1. temperatureunder reflux for 22 hours
  2. customThe solution was evaporated under vacuo
  3. additionIt was diluted with water
  4. extractionthe solution was extracted with CH2Cl2
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated to an oil
  8. customIt was chromatographed (CH2Cl2 /MeOH, 2-5%)

Sources & evidence

ORD record
ord-eb617010b0b044a0bf4beee044bbf93f
Source dataset
uspto-grants-1995_02
Patent number
US05389661

Reaction notes

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