Water → 5-methoxy-4-(2-methyl-5-phenylbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 2296975Notes

Reaction equation

HRID 2296975 reaction equation
[CH3:1][O:2][C:3]1[NH:4][C:5](=[O:8])[NH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]1([C:21]2[CH:22]=[CH:23][C:24]([CH3:29])=[C:25]([CH:28]=2)[CH2:26]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C(#N)C>[CH3:1][O:2][C:3]1[N:4]([CH2:26][C:25]2[CH:28]=[C:21]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:22]=[CH:23][C:24]=2[CH3:29])[C:5](=[O:8])[NH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 120565275-Phenyl-2-methylbenzylbromideHCID 1354997413H-1,2,4-Triazol-3-one, 1,2-dihydro-5-methoxy-2×

Product 1

HCID 183888525-methoxy-4-(2-methyl-5-phenylbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 44.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 626 mg (5.44 mmol) of 5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one (said compound is a known compound described in J. Chem. Soc. Perkin I, 2645 (1973) and this was produced according to the method described in this literature. In this literature, said compound is named as 3-methoxy-1,2,4-triazol-5(4H)-one) in 7 ml of dry acetonitrile was added 0.79 g (5.71 mmol) of potassium carbonate. To the mixture was added dropwise a solution of 1.42 g (5.44 mmol) of 5-phenyl-2-methylbenzylbromide in 20 ml of dry acetonitrile at 55° C. After the mixture was stirred at the same temperature for additional 5 hours, water was added to the reaction mixture and it was extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated. To the resultant solid residue (1.51 g) was added tert-butyl methyl ether and the solid was washed and ice-cooled. The solid was collected by filtration and dried to obtain 0.72 g (2.44 mmol) of 5-methoxy-4-(2-methyl-5-phenylbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one as white powder.

Workup

  1. customPerkin I, 2645 (1973) and this was produced
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. additionTo the resultant solid residue (1.51 g) was added tert-butyl methyl ether
  7. washthe solid was washed
  8. temperatureice-cooled
  9. filtrationThe solid was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-205e7247efd241c1870f4e54460f21a8
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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