Dimethylhydantoin → 3-(6-Chloro-n-hexyl)-5,5-dimethyl-hydantoin

HRID 1284085Notes

Reaction equation

HRID 1284085 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].C(=O)([O-])[O-].[K+].[K+].[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Cl>O>[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:4]1[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]1=[O:7]

Participants

5

Reactant 3

HCID 6491DimethylhydantoinHCID 11430Potassium CarbonateHCID 165511,6-Dichlorohexane

Product 1

HCID 214116503-(6-Chloro-n-hexyl)-5,5-dimethyl-hydantoin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

128 g of 5,5-dimethyl-hydantoin (1.0 mol), 69 g of anhydrous potassium carbonate (0.5 mol) and 775 g of 1,6-dichlorohexane are reacted at 132°-150°C internal temperature (external temperature 160°C) and the resulting water of reaction is removed continuously by azeotropic circulatory distillation. After 6 hours 25 minutes, the reaction is complete and the reaction mixture is filtered hot to remove the potassium chloride formed. The filtrate is concentrated on a rotary evaporator and dried to constant weight at 100°C and 10-1 mm Hg.

Workup

  1. customis removed continuously by azeotropic circulatory distillation
  2. filtrationthe reaction mixture is filtered hot
  3. customto remove the potassium chloride
  4. customformed
  5. concentrationThe filtrate is concentrated on a rotary evaporator
  6. customdried to constant weight at 100°C

Sources & evidence

ORD record
ord-99857d370092469a8a353b2f056ef584
Source dataset
uspto-grants-1976_08
Patent number
US03978076

Reaction notes

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