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

HRID 2306688Notes

Reaction equation

HRID 2306688 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-4e68f1eaddfe4f6487d97a98803e857d
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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