Hydrochloric Acid → HCID 12056523, compound

HRID 1883620Notes

Reaction equation

HRID 1883620 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH2:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:13]=[CH:12][C:11]=2[CH3:22])[C:5](=[O:8])[NH:6][N:7]=1.[C:23](=O)([O-])[O-].[K+].[K+].CI.CN(C)C=O.Cl>C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C>[OH:1][CH2:2][C:3]1[N:4]([CH2:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:13]=[CH:12][C:11]=2[CH3:22])[C:5](=[O:8])[N:6]([CH3:23])[N:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12056524HCID 12056524, compound

Product 1

HCID 12056523HCID 12056523, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

6.29 g (21.3 mmol) of 5-hydroxymethyl-4-(2-methyl-5-phenylbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 3.53 g (25.6 mmol) of potassium carbonate and 3.63 g (25.6 mmol) of methyl iodide were stirred for 4 hours at 60° C. in 38 mol of anhydrous N,N-dimethylformamide. To the reaction solution was added 200 ml of a 5 wt % hydrochloric acid aqueous solution, and this was extracted with ethyl acetate. The organic layer was washed with water, 5 wt % sodium bicarbonate solution, then, saturated saline, dried over anhydrous magnesium sulfate, then, concentrated. The residuie was subjected to silica gel column chromatography (eluant: hexane/ethyl acetate=1/1 (v/v), then, ethyl acetate), to obtain 6.52 g (21.2 mmol) of 5-hydroxymethyl-2-methyl-4-(2-methyl-5-phenylbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one.

Workup

  1. extractionthis was extracted with ethyl acetate
  2. washThe organic layer was washed with water, 5 wt % sodium bicarbonate solution
  3. dry with materialsaturated saline, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-67532427415149f79661004c432f0caf
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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