Triethylamine → 5,5-Dimethyl-3-{4-[(trifluoromethyl)sulfanyl]phenyl}imidazolidine-2,4-dione

HRID 899977Notes

Reaction equation

HRID 899977 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C:10]([CH3:16])([CH3:15])[C:11](OC)=[O:12].[F:17][C:18]([S:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1)([F:20])[F:19]>C1(C)C=CC=CC=1.C(OCC)C>[CH3:16][C:10]1([CH3:15])[NH:9][C:29](=[O:30])[N:28]([C:25]2[CH:24]=[CH:23][C:22]([S:21][C:18]([F:20])([F:17])[F:19])=[CH:27][CH:26]=2)[C:11]1=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27333921-Isocyanato-4-[(trifluoromethyl)sulfanyl]benzeneHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 132680685,5-Dimethyl-3-{4-[(trifluoromethyl)sulfanyl]phenyl}imidazolidine-2,4-dioneYield 95.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

5.12 ml of triethylamine and 2.8 g of methyl α-aminoisobutyrate hydrochloride are added to a solution of 4 g of 4-trifluoromethylsulfanylphenyl isocyanate in 40 ml of toluene, under an inert atmosphere of argon at a temperature in the region of 20° C. The mixture thus obtained is refluxed for 24 hours and then cooled to a temperature in the region of 20° C. The reaction mixture is concentrated to dryness under reduced pressure and the residue obtained is taken up in ethyl ether and filtered. 5.3 g of 5,5-dimethyl-3-(4-trifluoromethylsulfanylphenyl)-imidazolidine-2,4-dione are thus obtained, the characteristics of which product are as follows:

Workup

  1. customThe mixture thus obtained
  2. temperatureis refluxed for 24 hours
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  4. customthe residue obtained
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7b9e4615779349b6b2b44f2541a350a5
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

Loading…