Acetonitrile → HCID 53654791, compound

HRID 619520Notes

Reaction equation

HRID 619520 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2].[I-].C[CH:17]=[N+:18]=[CH:19]C.[C:21](#N)C>>[CH3:17][N:18]([CH2:19][C:12]1[N:11]2[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=[CH:9][C:10]2=[N:14][CH:13]=1)[CH3:21]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 11127069ethyl imidazo[1,2-a]pyridine-5-carboxylateHCID 21892197N,N-dimethylmethyleneammoniumiodide

Product 1

HCID 53654791HCID 53654791, compound

Procedure

To a solution of 1.90 g (10.0 mmol) of 5-ethoxycarbonylimidazo[1,2-a]pyridine in 40 ml of acetonitrile was added 2.41 g (13.0 mmol) of N,N-dimethylmethyleneammonium iodide. The mixture was heated for two hours under reflux. The solvent was distilled off. To the residue was added methylene chloride. The mixture was washed with an aqueous solution of sodium thiosulfate and an aqueous solution of sodium hydrogencarbonate, successively, dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate) to afford 1.496 g of the desired compound (60.6%, a pale yellow solid). This product was recrystallized from ethyl acetate to afford the desired compound (colorless crystals), m.p.117.0-118.0° C.

Workup

  1. temperatureThe mixture was heated for two hours
  2. temperatureunder reflux
  3. distillationThe solvent was distilled off
  4. additionTo the residue was added methylene chloride
  5. washThe mixture was washed with an aqueous solution of sodium thiosulfate
  6. dry with materialan aqueous solution of sodium hydrogencarbonate, successively, dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-a04a9cf33d4f4e48ad180a59596b8e17
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

Loading…