Potassium Carbonate → 4-Allyl-5-(4-chlorophenyl)-2-[(5-methyl-1H-imidazol-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714653Notes

Reaction equation

HRID 714653 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[CH3:8].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([CH2:22][CH:23]=[CH2:24])[C:18](=[O:21])[NH:19][N:20]=2)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:22]([N:17]1[C:16]([C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)=[N:20][N:19]([CH2:2][C:3]2[N:4]=[CH:5][NH:6][C:7]=2[CH3:8])[C:18]1=[O:21])[CH:23]=[CH2:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1224334-hydroxymethyl-5-methyl-1H-imidazoleHCID 497656025-(4-chlorophenyl)-4-allyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 674083404-Allyl-5-(4-chlorophenyl)-2-[(5-methyl-1H-imidazol-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.89 mmol) of 4-hydroxymethyl-5-methyl-1H-imidazole, 252 mg (1.07 mmol) of the compound from Example 12A and 370 mg (2.68 mmol) of potassium carbonate were dissolved in 4.5 ml of DMF and 4.5 ml of water, and the mixture was stirred in a microwave oven at 200° C. for 75 min. After cooling to RT, for work-up, the mixture was diluted with 10 ml of water and extracted twice with in each case 15 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: first cyclohexane/ethyl acetate 1:1, then dichloromethane/methanol 10:1). This gave 153 mg (52% of theory) of the target compound in a purity of 73%.

Workup

  1. extractionextracted twice with in each case 15 ml of ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel (mobile phase

Sources & evidence

ORD record
ord-d8f567438b7443f99e1eed963f0aed00
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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