Sodium hydride → HCID 66926049, compound

HRID 2405034Notes

Reaction equation

HRID 2405034 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:15])=[N:12][O:13][N:14]=1.[H-].[Na+].[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl>O1CCCC1.C(OCC)(=O)C>[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23][N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C:10]1[C:11]([NH2:15])=[N:12][O:13][N:14]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 7385314-(1H-benzimidazol-2-yl)-1,2,5-oxadiazol-3-amineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 66926049HCID 66926049, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 0.5 g of 4-(1H-benzoimidazol-2-yl)-furazan-3-ylamine (CAS 332026-86-5) (2.49 mmol; 1.0 eq.) in 15 mL of dry tetrahydrofuran cooled to 0° C. are added portionwise 0.075 g of sodium hydride (2.98 mmol; 1.2 eq.). After stirring for 10 min at 0-5° C., the resulting clear solution is treated with 0.54 mL of 2-(trimethylsilyl)ethoxymethyl chloride (2.91 mmol; 1.17 eq.). The reaction solution is stirred for 0.5 h at 0-5° C. and then diluted with 30 mL of ethyl acetate. The solution is washed with water (20 mL) and brine (20 mL), dried over magnesium sulfate, filtered and concentrated to dryness. The oily residue is triturated in diisopropylether (10 mL) and the solvent is removed under reduced pressure to give 0.78 g of the desired product as an off-white solid.

Workup

  1. stirringThe reaction solution is stirred for 0.5 h at 0-5° C.
  2. washThe solution is washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe oily residue is triturated in diisopropylether (10 mL)
  7. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-c0d8ae4c9152482d866810b0cdd0b875
Source dataset
uspto-grants-2014_08
Patent number
US08802858B2

Reaction notes

Loading…