Dimethylformamide → HCID 59128601, compound

HRID 1043324Notes

Reaction equation

HRID 1043324 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH:8]=[N:7][C:6]([C:9]([O-:11])=[O:10])=[N:5]1.[CH3:12][Si:13]([CH2:16][CH2:17][O:18]CCl)([CH3:15])[CH3:14].[CH3:21]N(C=O)C>>[CH3:21][O:10][C:9]([C:6]1[N:7]=[CH:8][N:4]([CH2:3][O:18][CH2:17][CH2:16][Si:13]([CH3:15])([CH3:14])[CH3:12])[N:5]=1)=[O:11]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 52987606HCID 52987606, compound

Product 1

HCID 59128601HCID 59128601, compoundYield 41%

Procedure

To a suspension of NaH (60% dispersion) (200 mg, 5.00 mmol) in DMF (5 mL) at 0° C., a solution of methyl-1H-1,2,4-triazolecarboxylate (635 mg, 5.00 mmol) in DMF (5 mL) was added dropwise. The resulting suspension was stirred at the same temperature for 30 min and treated with SEMCl (0.90 mL, 5.0 mmol). The resulting solution was stirred at RT for 30 min and poured onto ice. The product was extracted with ether (3×20 mL). The ether layers were combined, dried (Na2SO4) and concentrated in vacuo. The residue obtained was chromatographed on silica (10% EtOAc/hexane) to obtain the title compound (530 mg, 41%). Mass spectrum (ESI, m/z): Calcd. for C10H19N3O3Si, 258.1 (M+H). found 258.2.

Workup

  1. stirringThe resulting solution was stirred at RT for 30 min
  2. additionpoured onto ice
  3. extractionThe product was extracted with ether (3×20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas chromatographed on silica (10% EtOAc/hexane)

Sources & evidence

ORD record
ord-af31aa782fc44a6e8eb4799e04a645a5
Source dataset
uspto-grants-2013_10
Patent number
US08557847B2

Reaction notes

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