Formaldehyde → [(2,4-Dioxoimidazolidin-1-yl)methyl]phosphonic acid

A 500 ml round-bottom flask was equipped with a thermometer, condenser, magnetic stirrer, and heating mantle. Into the flask was charged, under nitrogen, 10.0 g (0.100 mole) of hydantoin, 3.2 g (0.10 mole) of paraformaldehyde (purity: ca 95%), and 60 ml of anhydrous acetic acid. The resulting mixture was heated at reflux for 0.75 hour and then cooled. To the resulting clear solution was added 8.5 g (0.100 mole) of 97% phosphorous acid and 30.6 g (0.300 mole) of acetic anhydride. The reaction mixture was heated to reflux over 1.2 hours and held at reflux for another 0.1 hour. (A white solid precipitated early in the heating period and then redissolved toward the end.) The reaction mixture was cooled somewhat, and 150 ml of water was added to it. The resulting solution was heated at reflux for 2.0 hours, cooled, and vacuum stripped at 70° C. to give 21.4 g of crude 1-(phosphonomethyl)hydantoin as an oil. Quantitative analysis by hplc showed the yield of 1-(phosphonomethyl) hydantoin to be 46%.

1. customA 500 ml round-bottom flask was equipped with a thermometer, condenser, magnetic stirrer
2. temperatureheating mantle
3. additionInto the flask was charged, under nitrogen
4. temperatureThe resulting mixture was heated
5. temperatureat reflux for 0.75 hour
6. temperaturecooled
7. temperatureThe reaction mixture was heated
8. temperatureto reflux over 1.2 hours
9. temperatureat reflux for another 0.1 hour
10. custom(A white solid precipitated early in the heating period
11. dissolutionredissolved toward the end
12. temperature) The reaction mixture was cooled somewhat
13. addition150 ml of water was added to it
14. temperatureThe resulting solution was heated
15. temperatureat reflux for 2.0 hours
16. temperaturecooled
17. customstripped at 70° C.

ORDレコード

ord-6033f85baadb4db3b3c61a3567442dd2

出典データセット

uspto-grants-1986_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04578224