Diethyl Ether → HCID 57089368, compound

HRID 903335Notes

Reaction equation

HRID 903335 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:10]([CH3:12])([CH3:11])[C:8](=[O:9])[N:7]([CH2:13][CH2:14][OH:15])[C:5]1=[O:6].[O:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C1[O:24]C1.[CH2:25]([O:27][CH2:28][CH3:29])[CH3:26]>>[OH:24][CH2:26][CH2:25][O:27][CH2:28][CH2:29][O:1][CH2:2][CH2:3][N:4]1[C:10]([CH3:12])([CH3:11])[C:8](=[O:9])[N:7]([CH2:13][CH2:14][O:15][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:16])[C:5]1=[O:6]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6354Ethylene Oxide3×HCID 312751,4-DioxaneHCID 1178792,4-Imidazolidinedione, 1,3-bis(2-hydroxyethyl)-5,5-dimethyl-

Product 1

HCID 57089368HCID 57089368, compound

Conditions

Temperature
15 °C

Procedure

A clear colourless solution is prepared at 60° C. from 108.1 g of 1,3-di(β-hydroxyethyl)-5,5-dimethylhydantoin (0.5 mol) [manufactured according to example 3], 500 ml of dioxan and 2 ml of a 47% strength boron trifluoride-diethyl etherate solution in diethyl ether. 88.1 g of ethene oxide (about 2 mols) are introduced into this solution over the course of 2 hours and 20 minutes. Here the procedure followed is to pass a constant ethene oxide gas stream of such strength into the solution that practically all the ethene oxide is absorbed. The amount of the ethene oxide introduced is continuously controlled by means of a suitable gas flow meter (rotameter). The reaction is weakly exothermic so that after removing the external heating the temperature of mixture rises about 10 degrees to 70° C. After stopping the stream of ethene oxide the mixture is cooled to 15° C. and treated with 15 ml of 50% strength sodium hydroxide solution. The mixture is filtered and the clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg) and thereafter treated at 80° C./0.1 mm Hg until constant weight is reached. An oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows, in addition to the absorption due to the dimethylhydantoin, a strong OH absorption (2.92-3.02μ) and a very strong C-O-C absorption (8.9-9.4μ). The molecular weight is determined by vapour pressure osmometry to be M=394 (theory =392.5), and elementary analysis shows 51.7% C and 8l4% H (calculated: 52.0% C and 8.2% H).

Workup

  1. customis absorbed
  2. additionThe amount of the ethene oxide introduced
  3. customthat after removing the
  4. temperatureexternal heating the temperature of mixture
  5. customrises about 10 degrees to 70° C
  6. additiontreated with 15 ml of 50% strength sodium hydroxide solution
  7. filtrationThe mixture is filtered
  8. concentrationthe clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg)
  9. additiontreated at 80° C./0.1 mm Hg until constant weight
  10. customAn oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows
  11. additionin addition
  12. customto the absorption due to the dimethylhydantoin
  13. customa strong OH absorption (2.92-3.02μ)
  14. customa very strong C-O-C absorption (8.9-9.4μ)

Sources & evidence

ORD record
ord-a627ff67c31740c7980d5f4afb26d651
Source dataset
uspto-grants-1980_10
Patent number
US04227005

Reaction notes

Loading…