Dimethylhydantoin → 3-Allyl-5,5-dimethylhydantoin

HRID 1706290

Reaction equation

HRID 1706290 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[CH2:10](Cl)[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:12]([N:4]1[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]1=[O:7])[CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 6491DimethylhydantoinHCID 7850Allyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 5976963-Allyl-5,5-dimethylhydantoin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

640.6 g (5 mols) of 5,5-dimethylhydantoin, 420.9 g (5 mols+10% excess) of allyl chloride, 380.1 g (2.5 mols+10% excess) of potassium carbonate and 1,000 ml of dimethylformamide are reacted, and worked up, analogously to Example 1. 820 g (97.5% of theory) of a brownish waxy crude product are obtained and are purified by distillation. 713.7 g (84.9% of theory) of a distillate are obtained; this boils at 114° C./13.3 Pas and melts at 66.2°-68.7° C.

Sources & evidence

ORD record
ord-defef1b04107402895f86efc4569fc4c
Source dataset
uspto-grants-1980_06
Patent number
US04206309

Linked notes

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