Sodium hydride → 1-Ethyl-4-methyl-3-(2-trimethylsilanylethoxymethyl)-1,3-dihydrobenzimidazol-2-one

HRID 1176615Notes

Reaction equation

[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([CH3:12])[C:6]=2[NH:5][C:4]1=[O:13])[CH3:2].[H-].[Na+].[CH3:16][Si:17]([CH3:24])([CH3:23])[CH2:18][CH2:19][O:20][CH2:21]Cl.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([CH3:12])[C:6]=2[N:5]([CH2:21][O:20][CH2:19][CH2:18][Si:17]([CH3:24])([CH3:23])[CH3:16])[C:4]1=[O:13])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3.500 g of 1-ethyl-4-methyl-1,3-dihydrobenzimidazol-2-one in 40 ml of anhydrous N,N-dimethylformamide is admixed at 0° C. with 0.874 g of sodium hydride dispersion (60%). The reaction mixture is stirred at 0° C. over a further 30 minutes and 4.06 ml of 2-(trimethylsilanyl)ethoxymethyl chloride are added dropwise. The reaction mixture is stirred at 20° C. over 14 hours, poured onto 150 ml of saturated aqueous sodium hydrogencarbonate solution and extracted with tert-butyl methyl ether (2×200 ml). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a brown oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (1:3 EtOAc-heptane); Rt=5.62.

Workup

stirringThe reaction mixture is stirred at 20° C. over 14 hours
extractionextracted with tert-butyl methyl ether (2×200 ml)
dry with materialThe combined organic phases are dried over sodium sulphate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-b32fc172baa34e178830c9338138107d
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842688B2

Reaction notes

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