Urea → 2,4-Imidazolidinedione, 5-cyclohexyl-

HRID 1978160Notes

Reaction equation

HRID 1978160 reaction equation
[CH:1]1([CH:7]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]([NH2:12])=[O:11].CN1CCC[C:15]1=[O:19]>[Pd](Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.S(=O)(=O)(O)O.[Br-].[Li+]>[CH:1]1([CH:7]2[NH:12][C:10](=[O:11])[NH:9][C:15]2=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 3

HCID 1176UreaHCID 13387N-methyl-2-pyrrolidoneHCID 16275Cyclohexanecarboxaldehyde

Product 1

HCID 38708432,4-Imidazolidinedione, 5-cyclohexyl-Yield 70%

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidCatalystHCID 11776TriphenylphosphineCatalystHCID 82050Lithium BromideCatalystHCID 83469Palladium bromide (PdBr2)Catalyst

Procedure

2,800 g cyclohexanecarbaldehyde, 1,500 g urea, 25 ml N-methylpyrrolidone, 0.017 g palladium(II) bromide, 0.033 g triphenylphosphane, 0.100 g sulfuric acid and 0.760 g lithium bromide are reacted in a 300 ml autoclave under 60 bar at 100C. After a reaction time of 12 hours, the solvent is removed in vacuo and the residue is analyzed by means of high pressure liquid chromatography (HPLC). 3,200 g 5-cyclohexyl-hydantoin are formed. This corresponds to a yield of 70%.

Workup

  1. customAfter a reaction time of 12 hours, the solvent is removed in vacuo

Sources & evidence

ORD record
ord-580fcdc3935949378a5ba7b115ad5962
Source dataset
uspto-grants-2001_05
Patent number
US06235910B1

Reaction notes

Loading…