Water → 4-[(5-Formylimidazol-1-yl)methyl]benzonitrile

HRID 989255Notes

Reaction equation

HRID 989255 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][C:10]1[N:14]([CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[CH:13]=[N:12][CH:11]=1.O>CS(C)=O>[CH:9]([C:10]1[N:14]([CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[CH:13]=[N:12][CH:11]=1)=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 101982471-(4-Cyanobenzyl)-5-hydroxymethyl-1H-imidazole

Product 1

HCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Triethylamine (13.8 ml/99.6 mmol) and then SO3-pyridine complex (9.89 g/62.25 mmol) are added in succession to a solution of 4.6 g (24.9 mmol) of the compound obtained in Step A in 120 ml of DMSO, and the reaction mixture is stirred at room temperature for 30 minutes. The whole is then brought to 0° C., hydrolysed with H2O, and then extracted several times with AcOEt. The organic phases are combined, washed with a saturated NaCl solution, dried over MgSO4, and evaporated to dryness to yield the title product.

Workup

  1. extractionextracted several times with AcOEt
  2. washwashed with a saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-33e48f36ca4d431ba48ac9364206d3df
Source dataset
uspto-grants-2003_10
Patent number
US06638962B2

Reaction notes

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