反应详情

温度

0 °C

To a solution of 1-(2-hydroxy-ethyl)-imidazolidin-2-one (1.00 g, 7.68 mmol) in acetone (70 ml) was added 15% aqueous sodium bicarbonate (21 ml) to give a white slurry, which was then cooled to 0° C. (JOC 2003, 68, 4999-5001). Sodium bromide (0.16 g, 1.54 mmol) and TEMPO (0.024 g, 0.15 mmol) were added and the resulting mixture was stirred for 10 minutes followed by the addition of trichloroisocyanuric acid (3.57 g, 15.4 mmol) in four equal portions added every five minutes. The pale yellow slurry was warmed to 25° C. and stirred for an additional 12 hours to yield a yellow solution. Iso-propanol (9 ml) was added and the mixture was stirred for 45 minutes to give a white slurry, which was filtered through a Celite® cake. The filtrate was concentrated in vacuo, quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (50 ml). The aqueous phase was acidified with 4N HCl until pH ˜2 and then put on for continuous extraction with 5% methanol in methylene chloride (˜120 ml) for 16 hours. The organic extract was dried over sodium sulfate, filtered and concentrated in vacuo to yield (2-oxo-imidazolidin-1-yl)-acetic acid (0.530 g, 48%) as a white solid.

1. customto give a white slurry, which
2. additionadded every five minutes
3. temperatureThe pale yellow slurry was warmed to 25° C.
4. stirringstirred for an additional 12 hours
5. customto yield a yellow solution
6. stirringthe mixture was stirred for 45 minutes
7. customto give a white slurry, which
8. filtrationwas filtered through a Celite® cake
9. concentrationThe filtrate was concentrated in vacuo
10. customquenched with saturated aqueous sodium bicarbonate
11. extractionextracted with ethyl acetate (50 ml)
12. extractionput on for continuous extraction with 5% methanol in methylene chloride (˜120 ml) for 16 hours
13. extractionThe organic extract
14. dry with materialwas dried over sodium sulfate
15. filtrationfiltered
16. concentrationconcentrated in vacuo