反应详情

Triethylamine (5.8 parts by weight) was added dropwise to a mixture of imidazolidin-2-on-1-carbonyl chloride (7.4 parts by weight), tetrahydrofurane (50 parts by volume) and cyclohexanol (5.5 parts by weight) while stirring, and cooling with ice, the mixture was then slowly stirred overnight at room temperature and subsequently boiled for 1 hour under reflux, and the triethylamine hydrochloride was filtered off hot. The filtrate was completely evaporated in vacuo, the residue was triturated with cyclohexane and the solid product was filtered off and dried 3 days in a desiccator. Yield: 5.0 parts by weight. This substance (5.0 parts by weight was then suspended in tetrahydrofurane, triethylamine (5.2 parts by volume) was added, the mixture was boiled under reflux and a solution of trimethylchlorosilane (3.8 parts by weight) in tetrahydrofurane (10 parts by volume) was at the same time added dropwise. Thereafter the mixture was boiled overnight under reflux and insoluble matter was then filtered off hot. A solution of phosgene (2.6 parts by weight) in tetrahydrofurane (10 parts by volume) was slowly added to the filtrate at room temperature and the mixture was left to stand well sealed at room temperature for 24 hours. A precipitate which was present (largely triethylamine hydrochloride) was then filtered off and the filtrate was completely evaporated in vacuo. The cyrstalline residue was dried in a desiccator. The substance has a broad absorption between 1680 and 1820 cm-1 in the carbonyl region of the IR-spectrum (Nujol). It was reacted, in this form, with ampicillin.

1. temperaturecooling with ice
2. temperatureunder reflux
3. filtrationthe triethylamine hydrochloride was filtered off hot
4. customThe filtrate was completely evaporated in vacuo
5. customthe residue was triturated with cyclohexane
6. filtrationthe solid product was filtered off
7. customdried 3 days in a desiccator
8. additiontriethylamine (5.2 parts by volume) was added
9. temperatureunder reflux
10. additionadded dropwise
11. waitThereafter the mixture was boiled overnight
12. temperatureunder reflux
13. filtrationinsoluble matter was then filtered off hot
14. additionA solution of phosgene (2.6 parts by weight) in tetrahydrofurane (10 parts by volume) was slowly added to the filtrate at room temperature
15. waitthe mixture was left
16. customto stand well sealed at room temperature for 24 hours
17. filtrationwas then filtered off
18. customthe filtrate was completely evaporated in vacuo
19. customThe cyrstalline residue was dried in a desiccator
20. customa broad absorption between 1680 and 1820 cm-1 in the carbonyl region of the IR-spectrum (Nujol)
21. customIt was reacted, in this form, with ampicillin