Water → HCID 15032033, compound

HRID 1650887Notes

Reaction equation

HRID 1650887 reaction equation
[CH2:1]([N:5]1[C:11]([CH3:13])([CH3:12])[C:9](=[O:10])[NH:8][C:6]1=[O:7])[C:2](=[CH2:4])[CH3:3].[H-].[Na+].[CH2:16](Cl)[C:17](=[CH2:19])[CH3:18].O>CN(C=O)C>[CH2:1]([N:5]1[C:11]([CH3:13])([CH3:12])[C:9](=[O:10])[N:8]([CH2:18][C:17](=[CH2:16])[CH3:19])[C:6]1=[O:7])[C:2](=[CH2:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 15065991HCID 15065991, compound

Product 1

HCID 15032033HCID 15032033, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
15 °C

Procedure

In a 100 ml three necked flask is placed 10 g (0.055 mol) of N-methallyl-5,5-dimethylhydantoin in 100 ml DMF under nitrogen. The solution is cooled to 15° C. and 2.7 g of sodium hydride/mineral oil is added. The reaction is stirred for 2 hours at 15° C. and then warmed to 25°C. Methallyl chloride (5.1 g, 0.056 mol) is added dropwise over 10 minutes, keeping the temperature at 30° C. The reaction is stirred overnight, then poured into 200 ml water, extracted with 2 X 100 ml ether and dried over magnesium sulfate. After removing the ether in vacuo, the residue is distilled under vacuum (BP 100°-105°0 C. 0.3 mm Hg) to give 11.9 g N,N'-bismethallyl-5,5-dimethylhydantoin.

Workup

  1. temperaturewarmed to 25°C
  2. customat 30° C
  3. stirringThe reaction is stirred overnight
  4. extractionextracted with 2 X 100 ml ether
  5. dry with materialdried over magnesium sulfate
  6. customAfter removing the ether in vacuo
  7. distillationthe residue is distilled under vacuum (BP 100°-105°0 C. 0.3 mm Hg)

Sources & evidence

ORD record
ord-f591da6403be4385a9aeffadf4a8fe75
Source dataset
uspto-grants-1990_05
Patent number
US04925938

Reaction notes

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