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

HRID 2296983Notes

Reaction equation

HRID 2296983 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+].Br[CH2:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21].O>C(#N)C.C(OCC)(=O)C>[CH:20]([C:19]1[CH:18]=[C:17]([CH:24]=[CH:23][CH:22]=1)[CH2:16][N:4]1[C:3]([O:2][CH3:1])=[N:7][NH:6][C:5]1=[O:8])=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 71278253-(Bromomethyl)benzaldehydeHCID 1354997413H-1,2,4-Triazol-3-one, 1,2-dihydro-5-methoxy-

Product 1

HCID 183888674-(3-formylbenzyl)-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 18.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.92 g (8.0 mmol) of 5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one in 15 ml of dry acetonitrile was added 1.16 g (8.4 mmol) of potassium carbonate. To the mixture was added dropwise a solution of 1.59 g of crude 3-(bromomethyl)benzaldehyde in 30 ml of dry acetonitrile at 55° C. under an atmosphere of nitrogen. After the mixture was stirred at the same temperature for additional 6 hours, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue (1.31 g) was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=1:1 and then 1:2) to obtain 0.35 g (1.50 mmol) of 4-(3-formylbenzyl)-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one as white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. washeluted with n-hexane

Sources & evidence

ORD record
ord-cf55b95f9ccd4d0f95c8cea049ec55de
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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