p-Toluenesulfonic acid monohydrate → 1-Methyl-5-(1,3-dioxolan-2-yl)-imidazole

HRID 1936763Notes

Reaction equation

HRID 1936763 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]=[CH:3]1.[OH2:9].[C:10]1([CH3:20])C=CC(S(O)(=O)=O)=CC=1>C(O)CO>[CH3:1][N:2]1[C:6]([CH:7]2[O:9][CH2:10][CH2:20][O:8]2)=[CH:5][N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 5735921-methyl-1H-imidazole-5-carbaldehyde

Product 1

HCID 226098451-Methyl-5-(1,3-dioxolan-2-yl)-imidazole

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

1-Methyl-5-formyl imidazole (0.64 g) was treated with ethylene glycol (0.3 ml), p-toluenesulphonic acid monohydrate (0.0015 g) and powdered 4A molecular seives under N2 for 18 hours at reflux. Subsequent cooling and filtration was followed by washing of the organic phase with aqueous sodium carbonate solution (2N), drying and concentration to give the title compound; δH (CDCl3) 7.43 (1H,s), 7.12 (1H,s), 5.91 (1H,s), 4.10(4H,m), 3.70(3H,s).

Workup

  1. customfor 18 hours
  2. temperatureat reflux
  3. temperatureSubsequent cooling
  4. filtrationfiltration
  5. washby washing of the organic phase with aqueous sodium carbonate solution (2N)
  6. customdrying
  7. concentrationconcentration

Sources & evidence

ORD record
ord-6d03490ed8024c9684f012036f469dc4
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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