Sodium hydride → HCID 68497212, compound

HRID 1176568Notes

Reaction equation

HRID 1176568 reaction equation
O[CH2:2][C:3]1[C:8]2[NH:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[N:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl>CN(C)C=O>[CH3:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[N:11]([CH2:23][O:22][CH2:21][CH2:20][Si:19]([CH3:26])([CH3:25])[CH3:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178499035HCID 178499035, compound

Product 1

HCID 68497212HCID 68497212, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The stirred solution of 1.60 g of methyl 7-hydroxymethyl-1H-benzoimidazole-2-carboxylate and 13.0 ml of N,N-dimethylformamide is admixed at 0° C. with 0.274 g of sodium hydride dispersion (55%) and, after 60 minutes, with 1.33 ml of 2-(trimethylsilyl)ethoxymethyl chloride. The mixture is stirred at room temperature over 3 hours, subsequently poured onto ice-water (100 ml) and extracted with tert-butyl methyl ether (2×100 ml). The organic phases are washed successively with water (100 ml) and brine (100 ml), dried over sodium sulphate and concentrated. The title compound is obtained as a white solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.23 (1:2 EtOAc-heptane); Rt=5.16; m.p. 59.6-59.8° C.

Workup

  1. additionsubsequently poured onto ice-water (100 ml)
  2. extractionextracted with tert-butyl methyl ether (2×100 ml)
  3. washThe organic phases are washed successively with water (100 ml) and brine (100 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-77b8a3352dbc451daec6426b2c9c558a
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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