Dimethylformamide → HCID 21395743, compound

HRID 1439505Notes

Reaction equation

HRID 1439505 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[Cl-].[Li+].CN(C)C=O.[CH:17]12[O:23][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22]2>CC(C)=O>[OH:23][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[N:4]1[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]1=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6491DimethylhydantoinHCID 9246Cyclohexene oxideHCID 433294Lithium Chloride

Product 1

HCID 21395743HCID 21395743, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 128.1 g of 5,5-dimethylhydantoin (1 mol), 1 g of lithium chloride and 200 ml of dimethylformamide is stirred at 100° C in a 500 ml glass apparatus having a stirrer, thermometer, dropping funnel and reflux condenser. 100 g of cyclohexene oxide (1.02 mols) are added dropwise to this solution over the course of 120 minutes, whilst stirring. Thereafter the mixture is stirred for a further 5 hours at 125°-130° C. After cooling to about 60° C, the reaction mixture is filtered and is concentrated to dryness on a rotary evaporator at 70° C under a waterpump vacuum. Thereafter the residue is dried to constant weight at 90° C/0.1 Hg. 217.8 g of a yellowish, crystalline material (96.4% of theory) are obtained, and this can be recrystallised, for example from acetone. The purified product melts at 159°-161° C. Elementary analysis shows the following values:

Workup

  1. temperaturereflux condenser
  2. stirringThereafter the mixture is stirred for a further 5 hours at 125°-130° C
  3. filtrationthe reaction mixture is filtered
  4. concentrationis concentrated to dryness on a rotary evaporator at 70° C under a waterpump vacuum
  5. customThereafter the residue is dried to constant weight at 90° C/0.1 Hg
  6. custom217.8 g of a yellowish, crystalline material (96.4% of theory) are obtained

Sources & evidence

ORD record
ord-037f8c784f974f50b7dae52a6ac73366
Source dataset
uspto-grants-1977_11
Patent number
US04060525

Reaction notes

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