Acetone → 3-(3-Chloro-4-trifluoromethoxyphenyl)-5,5-dimethyl-hydantoin

HRID 2413154Notes

Reaction equation

HRID 2413154 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[C:3]#N.[Cl:7][C:8]1[CH:9]=[C:10]([N:19]=[C:20]=[O:21])[CH:11]=[CH:12][C:13]=1[O:14][C:15]([F:18])([F:17])[F:16].CC(C)=[O:24]>>[Cl:7][C:8]1[CH:9]=[C:10]([N:19]2[C:3](=[O:24])[C:2]([CH3:6])([CH3:5])[NH:1][C:20]2=[O:21])[CH:11]=[CH:12][C:13]=1[O:14][C:15]([F:18])([F:17])[F:16]

Participants

4

Reactant 3

HCID 180AcetoneHCID 880222-Amino-2-methylpropionitrileHCID 15765405HCID 15765405, compound

Product 1

HCID 132680653-(3-Chloro-4-trifluoromethoxyphenyl)-5,5-dimethyl-hydantoin

Conditions

Temperature
45 °C

Procedure

6.5 g (0.077 mol) of α-aminoisobutyronitrile are added dropwise to a solution of 17.1 g (0.072 mol) of 3-chloro-4-trifluoromethoxyphenyl isocyanate in 100 ml of acetone. The temperature increases to about 45° C. during this procedure. After the reaction has ceased, the solvent is evaporated off in vacuo, and the residue is then boiled for 1 hour with 80 ml of semi-concentrated hydrochloric acid. The 3-(3-chloro-4-trifluoromethoxyphenyl)-5,5-dimethyl-hydantoin formed during this process is recrystallized from toluene with the addition of petroleum ether. 16 g of product of melting point 104°-107° C. are obtained.

Workup

  1. customthe solvent is evaporated off in vacuo

Sources & evidence

ORD record
ord-43698cb3927f4f9295e2b3bd6adb0a53
Source dataset
uspto-grants-1985_01
Patent number
US04496575

Reaction notes

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