Triethylamine → HCID 86010017, compound

HRID 1244314Notes

Reaction equation

HRID 1244314 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([OH:8])=O.C1N=CN([C:14](N2C=NC=C2)=[O:15])C=1.C([N:23]([CH2:26][CH3:27])CC)C.[C:28]1([C:34]2[CH:41]=[C:38](OC)[C:37](N)=[CH:36][CH:35]=2)[CH:33]=[CH:32][CH:31]=CC=1>CN(C=O)C>[CH3:14][O:15][C:31]1[CH:32]=[CH:33][C:28]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:41]=2)=[CH:27][C:26]=1[NH:23][C:6]([C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 420703-Methoxy[1,1'-biphenyl]-4-amineHCID 682631,1'-CarbonyldiimidazoleHCID 5743211H-Imidazole-2-carboxylic acid

Product 1

HCID 86010017HCID 86010017, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.31 g of imidazole-2-carboxylic acid (2.76 mmol) in 14 ml DMF was added 0.448 g of CDI (2.76 mmol), 0.38 ml triethylamine (2.76 mmol) and stirred at ambient temperature for 1 h. Then the mixture was refluxed for 30 min. After cooling to ambient temperature, 0.5 g of 5-phenyl-o-anisidine (2.5 mmol) was added and the reaction mixture was heated to reflux for 16 h. The mixture was evaporated and the residue taken up in water (40 ml) and extracted 3 times with methylene chloride. The combined organic phases were tried on sodium carbonate, evaporated and the residue was stirred in hot ethyl acetate. After filtration and drying, 0.11 g 1H-imidazole-2-carboxylic acid (4-methoxy-biphenyl-3-yl)-amide (14%) were obtained as a light yellow solid; M.p.: 276° C. 0.1 g of 1H-Imidazole-2-carboxylic acid (4-methoxy-biphenyl-3-yl)-amide (0.36 mmol) was taken up in toluene (5.0 ml) and treated with 0.435 g of Lawesson reagent (1.0 mmol). The reaction mixture was heated to reflux for 16 h. After cooling to ambient temperature, water (25 ml) was added and the mixture was extracted 3 times with dichloro methane. The combined organic phases were dried on sodium carbonate, evaporated and the residue triturated in methanol. 0.08 g of 1H-imidazole-2-carbothioic acid (4-methoxy-biphenyl-3-yl)-amide (73%) were obtained as a yellow solid; M.p.: 223–226° C.

Workup

  1. temperatureThen the mixture was refluxed for 30 min
  2. temperatureAfter cooling to ambient temperature
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 16 h
  5. customThe mixture was evaporated
  6. extractionextracted 3 times with methylene chloride
  7. customevaporated
  8. stirringthe residue was stirred in hot ethyl acetate
  9. filtrationAfter filtration
  10. customdrying

Sources & evidence

ORD record
ord-b877ad5a62414675bedfaf3dc4531473
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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