2-Chloroethyl vinyl ether → 3-[2-(Vinyloxy)-ethyl]-5-methyl-5-ethyl-hydantoin

HRID 1706285

Reaction equation

HRID 1706285 reaction equation
[CH3:1][C:2]1([CH2:9][CH3:10])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[CH:11]([O:13][CH2:14][CH2:15]Cl)=[CH2:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:11]([O:13][CH2:14][CH2:15][N:4]1[C:3](=[O:8])[C:2]([CH3:1])([CH2:9][CH3:10])[NH:6][C:5]1=[O:7])=[CH2:12]

Participants

5

Reactant 3

HCID 80742-Chloroethyl vinyl etherHCID 11430Potassium CarbonateHCID 821625-Ethyl-5-methylhydantoin

Product 1

HCID 202856223-[2-(Vinyloxy)-ethyl]-5-methyl-5-ethyl-hydantoin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 71.04 g (0.5 mol) of 5-methyl-5-ethylhydantoin, 55.94 g (0.5 mol+5% excess) of 2-chloroethyl vinyl ether, 36.28 g (0.25 mol+5% excess) of anhydrous potassium carbonate and 150 ml of dimethylformamide is stirred, analogously to Example 1, for 4 hours and 35 minutes at 122°-129° C. After completion of the reaction, the reaction mixture is filtered and the clear filtrate is concentrated on a rotary evaporator at 80° C. under vacuum from a waterpump. The residue is taken up in 200 ml of acetone, 2 g of active charcoal are added and the mixture is kept at the boil for 15 minutes. It is then filtered and the filtrate is concentrated on a rotary evaporator at 60° C. under vacuum from a waterpump. The residue is freed from non-volatile constituents at 60° C. and 0.5 mm Hg and 86.9 g (81.9% of theory) of a yellowish, viscous crude product are obtained. This is purified by distillation in a high vacuum and 80.34 g (75.7% of theory) of the desired product, of boiling point 132° C./0.2 mm Hg, are obtained.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe clear filtrate is concentrated on a rotary evaporator at 80° C. under vacuum from a waterpump
  4. addition2 g of active charcoal are added
  5. waitthe mixture is kept at the boil for 15 minutes
  6. filtrationIt is then filtered
  7. concentrationthe filtrate is concentrated on a rotary evaporator at 60° C. under vacuum from a waterpump
  8. customis freed from non-volatile constituents at 60° C.
  9. custom0.5 mm Hg and 86.9 g (81.9% of theory) of a yellowish, viscous crude product are obtained
  10. distillationThis is purified by distillation in a high vacuum and 80.34 g (75.7% of theory) of the desired product, of boiling point 132° C./0.2 mm Hg
  11. customare obtained

Sources & evidence

ORD record
ord-7a2e746716a5498dbdc4279ba4c49af9
Source dataset
uspto-grants-1980_06
Patent number
US04206309

Linked notes

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