Imidazole → 2-chloromethyl-1-(tetrahydro-furan-2-yl)-1H-imidazole hydrochloride

HRID 2101511Notes

Reaction equation

N1C=CN=C1.O1C=CCC1.[O:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:21][OH:22].O=S(Cl)[Cl:25].C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:21][OH:22].[ClH:25].[Cl:25][CH2:21][C:17]1[N:16]([CH:12]2[CH2:13][CH2:14][CH2:15][O:11]2)[CH:20]=[CH:19][N:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

[1-(Tetrahydro-furan-2-yl)-1H-imidazol-2-yl]-methanol was prepared from imidazole and dihydrofuran according to a procedure in the literature (Song et al. J. Org Chem. 1999, 64, 1859-1867). To a solution of [1-(tetrahydro-furan-2-yl)-1H-imidazol-2-yl]-methanol (7.0 g, 41.7 mmol) in dry CH2Cl2 (80 mL) at 0° C. under N2 was added dropwise SOCl2. The resulting solution was stirred at 0° C. for 3 h and allowed to warm up gradually to ambient temperature overnight. The mixture was cooled in a dry ice-ethylene glycol bath before saturated NaHCO3 (200 mL) was added carefully. The resulting mixture was extracted with CH2Cl2 (3×100 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo. The crude 2-chloromethyl-1-(tetrahydro-furan-2-yl)-1H-imidazole hydrochloride (5.7 g, 74%) was obtained as a brown oil; ESI MS m/z 187 [C8H11ClN2O+H]+. The product was used immediately in the next reaction.

Workup

temperatureto warm up gradually to ambient temperature overnight
additionwas added carefully
extractionThe resulting mixture was extracted with CH2Cl2 (3×100 mL)
dry with materialThe combined extracts were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-dd3c069349974917ae2ec879fe829ea1
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572921B2

Reaction notes

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