Iodoethane → 1-ethyl-2-naphthalen-1-yl-1H-imidazole

HRID 12461Notes

Reaction equation

[H-].[Na+].[C:3]1([C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.I[CH2:19][CH3:20]>CN(C=O)C>[CH2:19]([N:17]1[CH:16]=[CH:15][N:14]=[C:13]1[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)[CH3:20]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of sodium hydride (2.40 g, 60% mineral oil suspension, 60 mmol) in anhydrous DMF (30 ml) is added a solution of 2-naphthalen-1-yl-1H-imidazole (9.70 g, 50 mmol) in DMF (70 ml) at rt. The resulting mixture is stirred at 50° C. for 1 hr, and then cooled to 0° C., after which iodoethane (8.19 g, 52.5 mmol, 1.05 eq.) is added dropwise. The mixture is stirred at rt for 1 hr, and then heated to 50° C. and stirred for an additional 8 hr. The reaction mixture is cooled to rt, and poured into ice-water (500 ml). The mixture is extracted with EtOAc (100 ml×3). The combined organic layers are washed with water and brine, dried over anhydrous sodium sulfate, and solvent is evaporated at reduced pressure. The crude product is purified by flash chromatography on silica gel to give the title compound. LCMS 223 (M+1).

Workup

temperaturecooled to 0° C.
stirringThe mixture is stirred at rt for 1 hr
temperatureheated to 50° C.
stirringstirred for an additional 8 hr
temperatureThe reaction mixture is cooled to rt
extractionThe mixture is extracted with EtOAc (100 ml×3)
washThe combined organic layers are washed with water and brine
dry with materialdried over anhydrous sodium sulfate, and solvent
customis evaporated at reduced pressure
customThe crude product is purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-80f85a55b5bb42a9b5fddbc41a2802c1
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728009B1

Reaction notes

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