Hydrochloric Acid → 3-(2-Aminoethyl)imidazolidine-2,4-dione hydrochloride

Temperature

100 °C

(2-Aminoethyl)-carbamic acid tert-butyl ester (14.4 g, 90 mmol) was dissolved in DCM (100 mL) and was treated with a solution of isocyanatoacetic acid ethyl ester (11.6 g. 90 mmol) in DCM (100 mL) added dropwise over 30 min. The resulting solution was stirred for 1 h and concentrated to give a pale gum. Aqueous 5N HCl (250 mL) was added and the mixture stirred until dissolved. The resulting solution was heated at 100° C. for 16 h, concentrated, water (250 mL) was added and the solution again concentrated to give a solid. Ethanol (100 mL) was added and the mixture was again concentrated. Ethanol (150 mL) was added and the mixture stirred for 16 h to give the product as a fine white powder which was collected by filtration. Yield=14.7 g, 91%. MS (M+H)+ 144.

1. additionadded dropwise over 30 min
2. concentrationconcentrated
3. customto give a pale gum
4. stirringthe mixture stirred
5. dissolutionuntil dissolved
6. concentrationconcentrated
7. additionwater (250 mL) was added
8. concentrationthe solution again concentrated
9. customto give a solid
10. concentrationthe mixture was again concentrated
11. additionEthanol (150 mL) was added
12. stirringthe mixture stirred for 16 h

ORD record

ord-5fd3537dd5034723bc2a04784c86f0ac

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858785B2