Triethylamine → Methyl-phenyl-carbamic Acid quinoxalin-2-yl Ester

HRID 1179853Notes

Reaction equation

HRID 1179853 reaction equation
[OH:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[I-].C[N+]1C=CN([C:19](=[O:28])[N:20]([CH3:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)C=1.C(N(CC)CC)C>C(#N)C>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:10]=[CH:11][C:2]=1[O:1][C:19](=[O:28])[N:20]([CH3:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109478841-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodideHCID 178516710HCID 178516710, compound

Product 1

HCID 69519306Methyl-phenyl-carbamic Acid quinoxalin-2-yl EsterYield 77.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-hydroxyquinoxaline (0.44 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 40° C. for 24 hours. 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 (0.65 g, 77% yield) as a white solid.

Workup

  1. temperatureby heating at 40° C. for 24 hours
  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-1a48193cb5b14110bc3520437c34aa51
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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