Sodium hydride → 3-(4-Bromophenyl)-1-methyl-4-[[2-(trimethylsilyl)ethoxy]methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one

HRID 1772607Notes

Reaction equation

HRID 1772607 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11](=[O:13])[N:10]([CH3:14])[N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:17][Si:18]([CH3:25])([CH3:24])[CH2:19][CH2:20][O:21][CH2:22]Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:22][O:21][CH2:20][CH2:19][Si:18]([CH3:25])([CH3:24])[CH3:17])[C:11](=[O:13])[N:10]([CH3:14])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 1369420733-(4-Bromophenyl)-1-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one

Product 1

HCID 1317341763-(4-Bromophenyl)-1-methyl-4-[[2-(trimethylsilyl)ethoxy]methyl]-4,5-dihydro-1H-1,2,4-triazol-5-oneYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 10b (1.00 g, 3.94 mmol) in DMF (5 mL) was added sodium hydride (200 mg, 5.00 mmol) in portions at 0° C., and the mixture was stirred for 20 min before 2-(trimethylsilyl)ethoxymethyl chloride (730 mg, 4.37 mmol) was added. The reaction mixture was stirred at rt overnight, and was quenched with H2O (50 mL). The resulting mixture was extracted with DCM (2×50 mL). The combined organic layers were dried over Na2SO4, filtered concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/petroleum ether (1:5 v/v) to obtain compound 10c as a yellow solid (600 mg, 40% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C15H22BrN3O2Si: 383.1 (M+H). Found 383.1.

Workup

  1. additionwas added
  2. customwas quenched with H2O (50 mL)
  3. extractionThe resulting mixture was extracted with DCM (2×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with EtOAc/petroleum ether (1:5 v/v)

Sources & evidence

ORD record
ord-1aa42f8c454145a6a697348cad9a183a
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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