Methyl 4-(chloromethyl)benzoate → Methyl 4-((1-methyl-3,5-dioxo-1,2,4-triazolidin4-yl)methyl)benzoate

HRID 1180112

Reaction equation

HRID 1180112 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[NH:5][C:4](=[O:8])[NH:3]1.[Na].[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1>CS(C)=O>[CH3:1][N:2]1[C:6](=[O:7])[N:5]([CH2:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]([O:11][CH3:10])=[O:21])=[CH:14][CH:15]=2)[C:4](=[O:8])[NH:3]1

Participants

5

Reactant 3

HCID 36664Methyl 4-(chloromethyl)benzoateHCID 1792121-Methyl-1,2,4-triazolidine-3,5-dioneHCID 5360545Sodium

Product 1

HCID 58978277Methyl 4-((1-methyl-3,5-dioxo-1,2,4-triazolidin4-yl)methyl)benzoateYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-methyl-[1,2,4]triazolidine-3,5-dione (1.886 g, 0.0164 mol) and sodium hyhride (200 mg) in DMSO (5 mL) was added 4-chloromethyl-benzoic acid methyl ester (1.0 g, 0.0054 mol). The mixture was stirred at RT for overnight, quenched with H2O (100 mL), and extracted by CH2Cl2. The organic layer was washed with H2O, dried (Na2SO4) and concentrated in vacuo to yield methyl 4-((1-methyl-3,5-dioxo-1,2,4-triazolidin4-yl)methyl)benzoate (1.02 g, 72%). 1H NMR (CDCl3): 7.93 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 4.68 (s, 2H), 3.83 (s, 3H), 3.27 (s, 3H). MS (ESI) m/e: 264 (M++1)

Workup

  1. customquenched with H2O (100 mL)
  2. extractionextracted by CH2Cl2
  3. washThe organic layer was washed with H2O
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b1ba69038d7549e4a387c422e77bffbb
Source dataset
uspto-grants-2007_10
Patent number
US07279576B2

Linked notes

Loading…