Potassium Carbonate → HCID 178497711, compound

HRID 1468190Notes

Reaction equation

HRID 1468190 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=O.C([O-])([O-])=O.[K+].[K+].Cl.[CH3:20][O:21][C:22](=[O:33])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30](=[NH:32])[NH2:31])[CH:24]=1.Cl.C(CC1C=C(C=CC=1)C(N)=O)(=N)N>C1COCC1.O>[CH3:20][O:21][C:22](=[O:33])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30]2[NH:31][CH:2]=[C:3]([C:5]3[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=3)[N:32]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 986544-(Bromoacetyl)benzonitrileHCID 86672754HCID 86672754, compound

Product 1

HCID 178497711HCID 178497711, compoundYield 129.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Suspend 4-(2-bromo-acetyl)-benzonitrile (0.11 g, 0.48 mmol), K2CO3 (0.28 g, 2.00 mmol) and a 2:1 mixture of 3-carbamimidoylmethyl-benzoic acid methyl ester hydrochloride/3-carbamimidoylmethyl-benzamide hydrochloride (0.14 g) into 5 mL of 4:1 THF/H2O. Heat the mixture to reflux for 2 h. Concentrate the mixture to dryness and dissolve into 20 mL of H2O. Add 5% aq HCl until pH is acidic. Extract with 2×20 mL of CH2Cl2. Dry organic phase with MgSO4, filter and concentrate to give 0.13 g of crude 3-[4-(4-cyano-phenyl)-1H-imidazol-2-ylmethyl]-benzoic acid methyl ester and 3-[4-(4-cyano-phenyl)-1H-imidazol-2-ylmethyl]-benzamide as a purple residue.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 2 h
  3. concentrationConcentrate the mixture to dryness
  4. dissolutiondissolve into 20 mL of H2O
  5. additionAdd 5% aq HCl until pH
  6. extractionExtract with 2×20 mL of CH2Cl2
  7. filtrationDry organic phase with MgSO4, filter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-d2165bda718b4f428c2168565a28a4b9
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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