Sodium hydride → HCID 59128604, compound

HRID 1991997Notes

Reaction equation

HRID 1991997 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[N:11]=[C:10]([Cl:12])[NH:9][N:8]=1)=[O:6].[CH3:13][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>CN(C=O)C>[CH3:3][O:4][C:5]([C:7]1[N:11]=[C:10]([Cl:12])[N:9]([CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[N:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 13989241Methyl 5-chloro-1H-1,2,4-triazole-3-carboxylate

Product 1

HCID 59128604HCID 59128604, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (60% dispersion, 53.9 mg, 1.34 mmol) in DMF (5 mL) at 0° C., a solution of 5-chloro-1H-[1,2,4]-triazole-3-carboxylic acid methyl ester (Bull. Pharm. Sci., 20(1): 47-61, (1997), 218 mg, 1.35 mmol) in DMF (10 mL) was added dropwise. The resulting suspension was stirred at the same temperature for 30 min and then treated with SEMCl (0.24 mL, 1.4 mmol). The resulting solution was stirred at RT for 30 min and poured onto ice. The mixture was extracted with ether (3×20 mL) and 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 (227 mg, 58%). Mass spectrum (ESI, m/z): Calcd. for C10H18ClN3O3Si, 292.0 and 294.0 (M+H), found 291.5 and 293.6.

Workup

  1. stirringThe resulting solution was stirred at RT for 30 min
  2. additionpoured onto ice
  3. extractionThe mixture 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-29c98c5f37d84ebb9a37dcd4ff5447c3
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

Loading…