N,N-Dimethylethylenediamine → HCID 68773949, compound

HRID 2191076Notes

Reaction equation

HRID 2191076 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[CH3:9][N:10]([CH3:14])[CH2:11][CH2:12][NH2:13]>C(OCCO)C.CCOC(C)=O>[CH3:9][N:10]([CH3:14])[CH2:11][CH2:12][NH:13][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 68773949HCID 68773949, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 8076Glycol monoethyl etherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 2-chloro-5-iodopyridine (0.50 g, 2.18 mmol) and N,N-dimethylethylenediamine (0.81 g, 1.00 mL, 9.20 mmol) in 2-ethoxyethanol (5 mL) was heated in a sealed tube under microwave irradiation at 125° C. for 1 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 oil was purified by column chromatography (SiO2, 3:1 EtOAc/MeOH) to give the title compound (0.22 g, 36%) as a viscous oil which solidified on standing. δH (CDCl3) 8.19 (1H, br. s), 7.53 (1H, m), 6.23 (1H, m), 3.29 (2H, m), 2.52 (2H, m), 2.24 (6H, s). Exchangeable proton not observed. LCMS (ES+) 292.0 (M+H)+.

Workup

  1. washwashed with water (3×20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residual oil was purified by column chromatography (SiO2, 3:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-e24a3722dfe840dbaef9b7118de69183
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

Loading…