Dimethylformamide → HCID 12801559, compound

Temperature

50 °C

To a solution of 21.5 g. (0.14 mole) of 2-phenylimidazole in 60 ml. dry dimethylformamide and 300 ml. dry tetrahydrofuran under nitrogen atmosphere there is added at room temperature 9.0 g. (0.19 mole) of 50% sodium hydride/mineral oil suspension. The resulting mixture is stirred and heated to 50° C. for about 3 hours. After cooling to room temperature the resulting mixture is treated dropwise with a solution of 40.5 g. (0.18 mole) of (±)-1-bromo-3,7-dimethyloctane in dry tetrahydrofuran. The reaction mixture is stirred over night at room temperature and the resulting mixture is filtered and the residue washed with tetrahydrofuran. The combined filtrate is concentrated in vacuo to an oil, the oil is then dissolved in methylene chloride, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield an oily product. Distillation gave (±)-1-(3,7-dimethyloctyl)-2-phenylimidazole; b.p. 150° to 157° C. at 0.2-0.16 mm.

1. temperatureAfter cooling to room temperature the resulting mixture
2. additionis treated dropwise with a solution of 40.5 g
3. stirringThe reaction mixture is stirred over night at room temperature
4. filtrationthe resulting mixture is filtered
5. washthe residue washed with tetrahydrofuran
6. concentrationThe combined filtrate is concentrated in vacuo to an oil
7. dissolutionthe oil is then dissolved in methylene chloride
8. washwashed with water
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customto yield an oily product
13. distillationDistillation

ORD record

ord-5e5df78985084d2aa89d056829b3fcb7

Source dataset

uspto-grants-1981_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04301170