Dimethyl(methylene)ammounium iodide → HCID 68777855, compound

HRID 2191075Notes

Reaction equation

HRID 2191075 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[CH3:11][N+:12]([CH3:14])=[CH2:13].[I-]>C1COCC1.CCOC(C)=O>[CH3:11][N:12]([CH2:14][C:8]1[N:6]2[CH:7]=[C:2]([I:1])[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1)[CH3:13]

Participants

5

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 27643276-Iodoimidazo(1,2-a)pyridine

Product 1

HCID 68777855HCID 68777855, compoundYield 135.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 6-iodoimidazo[1,2-a]pyridine (2.0 g, 8.2 mmol) and Eschenmoser's salt (5.0 g, 2.7 mmol) in THF (50 mL) was heated to reflux for 24 h. The reaction mixture was then diluted with EtOAc (50 mL), washed with water (3×20 mL), dried (MgSO4), filtered and concentrated in vacuo. The residual solid was triturated from Et2O, collected by filtration and dried to give the title compound (1.1 g, 45%) as a brown powder. δH (DMSO-d6) 8.67 (1H, m), 7.45 (1H, s), 7.43-7.41 (2H, m), 3.72 (2H, s), 2.14 (6H, s). LCMS (ES+) 302.2 (M+H)+.

Workup

  1. temperatureto reflux for 24 h
  2. washwashed with water (3×20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residual solid was triturated from Et2O
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-560fe5c969ef42688fbc7f7b4a2e7127
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

Loading…