Water → HCID 67024392, compound

HRID 1028479Notes

Reaction equation

HRID 1028479 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:8]=1)[CH2:2][CH3:3].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]([C:33]#[N:34])=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.CN(C)C(=O)C.C1(C)C=CC=CC=1>[C:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:8]2[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:5]=[C:4]2[CH2:1][CH2:2][CH3:3])=[CH:26][CH:25]=1)#[N:34]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 102860151H-Imidazole-4,5-dicarboxylic acid, 2-propyl-, 4,5-diethyl ester

Product 1

HCID 67024392HCID 67024392, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1140TolueneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
55 °C

Procedure

Diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate (30.7 g) obtained in Example 2 and 4′-(bromomethyl)biphenyl-2-carbonitrile (33.4 g) were dissolved in a mixture of acetone (45 ml) and N,N-dimethylacetamide (45 ml), followed by addition of potassium carbonate (29.3 g) to the reaction solution, and the reaction solution was stirred at 55° C. for 2 hours. The reaction solution was cooled to room temperature, followed by addition of water and toluene, and the organic layer was washed with water. The solvent was evaporated under reduced pressure to afford the title compound (53.8 g) as yellow crystals.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. washthe organic layer was washed with water
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-527f2fe0b8b945df8ccf707a9659b5c3
Source dataset
uspto-grants-2014_05
Patent number
US08735598B2

Reaction notes

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