Methylamine → (1-Methyl-4-phenyl-1H-imidazol-5-YL)methanol

HRID 32507Notes

Reaction equation

HRID 32507 reaction equation
[CH3:1][NH2:2].C1O[CH:7]([OH:9])[CH2:6]OC1O.[N+:11]([CH:13]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)S(C1C=CC(C)=CC=1)(=O)=O)#[C-:12]>C1COCC1>[CH3:1][N:2]1[C:6]([CH2:7][OH:9])=[C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:11]=[CH:12]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 186078Glycolaldehyde dimerHCID 10967613a-Tosylbenzyl isocyanide

Product 1

HCID 17965886(1-Methyl-4-phenyl-1H-imidazol-5-YL)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylamine (33% in industrial methylated spirits, 60.3 mL) was added to a solution of glycolaldehyde dimer (2.7 g) in THF (320 mL). After 75 minutes 1-{[isocyano(phenyl)methyl]sulfonyl}-4-methylbenzene (PhTosMIC) (Org. Syn., 77, 198-205) (10.8 g) was added, cooling to keep the reaction temperature below 30° C. The reaction was stirred for 90 minutes and the solvent evaporated to a volume of 100 mL. Water (500 mL) was added, and the title compound (4.94 g, 66%) collected by filtration as a white solid. The filtrate was extracted into EtOAc, dried, and the solvent removed in vacuo. The residue was triturated with EtOAc to give a further 1.06 g (14%) as a white solid.

Workup

  1. temperaturecooling
  2. customthe reaction temperature below 30° C
  3. customthe solvent evaporated to a volume of 100 mL
  4. additionWater (500 mL) was added
  5. filtrationthe title compound (4.94 g, 66%) collected by filtration as a white solid
  6. extractionThe filtrate was extracted into EtOAc
  7. customdried
  8. customthe solvent removed in vacuo
  9. customThe residue was triturated with EtOAc
  10. customto give a further 1.06 g (14%) as a white solid

Sources & evidence

ORD record
ord-8a42de69d6014efaa40cce829552abd2
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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