Ammonia → HCID 178421658, compound

A mixture of 387 g. bromomethyl 1-methylcyclohexyl ketone and 1000 ml. formamide was heated with stirring. A stream of ammonia was passed through the reaction mixture over a period of 1 hour, the mixture being maintained at a temperature of 140°-160°C. After the passage of ammonia had been completed the reaction mixture was heated to 180°-190°C. The reaction mixture was maintained at this temperature for a period of 2 hours. Excess of formamide was evaporated under reduced pressure and the residue diluted with a little warm water and made alkaline with potassium carbonate. The resulting mixture was extracted with ether. After separation the ethereal extract was washed with water, dried over sodium sulphate, evaporated and distilled to give the novel intermediate 4-(1-methylcyclohexyl)imidazole, b.p. 146°-148°C./0.2 mm. Hg. The distillate crystallized from petroleum ether (b.p. 60°-80°C.) to give the product, m.p. 73°-75°C.

1. additionA mixture of 387 g
2. temperaturethe mixture being maintained at a temperature of 140°-160°C
3. temperaturewas heated to 180°-190°C
4. temperatureThe reaction mixture was maintained at this temperature for a period of 2 hours
5. customExcess of formamide was evaporated under reduced pressure
6. additionthe residue diluted with
7. temperaturea little warm water
8. extractionThe resulting mixture was extracted with ether
9. customAfter separation the ethereal
10. extractionextract
11. washwas washed with water
12. dry with materialdried over sodium sulphate
13. customevaporated
14. distillationdistilled

ORD record

ord-d179b5fdc35140df9daa99d082c9b3ed

Source dataset

uspto-grants-1976_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03940484