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

HRID 1741490Notes

Reaction equation

HRID 1741490 reaction equation
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.CCOC(C)=O>CS(C)=O>[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH:13]=[O:14])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 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

To a solution of 1-(4-Cyanobenzyl)-5-(hydroxymethyl)-imidazole (21.5 g, 101 mmol) in DMSO (500 ml) at room temperature was added triethylamine (56 ml, 402 mmol), then SO3 -pyridine complex (40.5 g, 254 mmol). After 45 min, the reaction was poured into EtOAc, washed with water and brine, dried (Na2SO4), and concentrated in vacuo to provide the aldehyde as a white powder which was sufficiently pure without further purification.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7626f90b655479f9cc89e6c93fbd9d3
Source dataset
uspto-grants-1999_10
Patent number
US05972984

Reaction notes

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