Triethylamine → HCID 69519842, compound

HRID 1831230Notes

Reaction equation

HRID 1831230 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[I-].C[N+]1C=CN([C:20](=[O:29])[N:21]([CH3:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)C=1.C(N(CC)CC)C>C(#N)C>[CH3:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([O:1][C:20](=[O:29])[N:21]([CH3:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109478841-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodideHCID 178429252HCID 178429252, compound

Product 1

HCID 69519842HCID 69519842, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-hydroxy-4-methylquinoline (0.48 g, 3.00 mmol) ), 1-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodide (1.03 g, 3.00 mmol) and triethylamine (0.42 ml, 3.00 mmol) in acetonitrile (15 ml) was stirred at room temperature for 18 hours followed by heating at 50° C. for 4 days. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (30:70)) yielding the title compound (0.24 g, 27% yield) as a white solid.

Workup

  1. temperatureby heating at 50° C. for 4 days
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (30:70))

Sources & evidence

ORD record
ord-75e996fc9e95475eaea29a6051088f19
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

Loading…