Thionyl Chloride → 2-chloromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole hydrochloride

HRID 724447Notes

Reaction equation

S(Cl)([Cl:3])=O.[CH3:5][Si:6]([CH3:19])([CH3:18])[CH2:7][CH2:8][O:9][CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[C:12]1[CH2:16]O>C(Cl)(Cl)Cl>[ClH:3].[Cl:3][CH2:16][C:12]1[N:11]([CH2:10][O:9][CH2:8][CH2:7][Si:6]([CH3:19])([CH3:18])[CH3:5])[CH:15]=[CH:14][N:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of thionyl chloride (0.87 mL, 12.0 mmol, 3.0 eq) in chloroform (8 mL) was cooled to 0° C. and treated with a solution of [1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanol (0.92 g, 4.0 mmol, 1.0 eq) in chloroform (2 mL). The clear solution was stirred at 0° C. for 30 minutes and then at room temperature for 2 hours. The solvent was removed and the product was sequentially slurried and concentrated using chloroform, toluene and cyclohexane to give 2-chloromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole hydrochloride as a beige solid (1.1 g, 97%): 1H NMR (300 MHz, DMSO-d6) δ 7.85 (d, 1H, J=1.9 Hz), 7.70 (d, 1H, J=1.9 Hz), 5.62 (s, 2H), 5.14 (s, 2H), 3.57 (t, 2H, J=8.3 Hz), 0.90 (t, 2H, J=8.3 Hz), −0.02 (s, 9H); 13C NMR (75 MHz, DMSO-d6) δ 142.1, 123.2, 120.2, 76.5, 66.8, 31.7, 17.3, −1.4.

Workup

waitat room temperature for 2 hours
customThe solvent was removed
concentrationconcentrated

Sources & evidence

ORD record: ord-ed86a3b7d6d34041ad7f14514c9e4979
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141587B2

Reaction notes

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