Cyanamide → 4-tert-butyl-1H-imidazol-2-amine

Temperature

90 °C

To a stirred solution of 6.8 g of aminomethyl-(1,1-dimethylethyl)ketone, as the hydrochloride salt, in 30 ml of water were added portionwise 5.0 g of cyanamide. The pH of the reaction mixture was adjusted to 6.0 with 1N sodium hydroxide, and then the mixture was heated to 90° C. and stirred for fifty-five minutes. The reaction mixture was next cooled to room temperature, diluted with 100 ml. of water, and extracted several times with diethyl ether. The aqueous layer was made alkaline with ammonium hydroxide, and again extracted several times with diethylether. The extracts from the alkaline mixture were combined and concentrated to dryness to provide a solid residue. The residue thus obtained was dissolved in 20 ml of 6N hydrochloric acid and heated at reflux for sixteen hours. The reaction mixture was cooled, concentrated to an oil by evaporation of the solvent, and the oil was dissolved in water and made alkaline to pH 8.5. The alkaline mixture was extracted several times with diethyl ether. The etheral extracts were combined, washed with water, dried, and the solvent was removed by evaporation under reduced pressure to provide 0.5 g of 5-(1,1-dimethylethyl)-2-aminoimidazole.

1. temperatureThe reaction mixture was next cooled to room temperature
2. additiondiluted with 100 ml
3. extractionof water, and extracted several times with diethyl ether
4. concentrationconcentrated to dryness
5. customto provide a solid residue
6. customThe residue thus obtained
7. temperatureheated
8. temperatureat reflux for sixteen hours
9. temperatureThe reaction mixture was cooled
10. concentrationconcentrated to an oil by evaporation of the solvent
11. dissolutionthe oil was dissolved in water
12. extractionThe alkaline mixture was extracted several times with diethyl ether
13. washwashed with water
14. customdried
15. customthe solvent was removed by evaporation under reduced pressure

ORD record

ord-0c8749dcc20848e7bfede7e02174bd1b

Source dataset

uspto-grants-1985_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04515625