Water → 4-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile

HRID 468571Notes

Reaction equation

HRID 468571 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[CH3:14][C:15]1([CH3:22])[NH:19][C:18](=[O:20])[NH:17][C:16]1=[O:21].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:14][C:15]1([CH3:22])[C:16](=[O:21])[N:17]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=2)[C:18](=[O:20])[NH:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 6491DimethylhydantoinHCID 11430Potassium CarbonateHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrile

Product 1

HCID 111622854-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrileYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-fluoro-2-(trifluoromethyl)benzonitrile (5.67 g, 30 mmoles), 5,5-dimethyl-hydantoin (7.68 g, 60 mmoles), K2CO3 (8.28 g, 60 mmoles) in DMF (45 ml) is distributed in equal parts into three tubes to be placed in a microwave oven. Under magnetic stirring, each tube is irradiated at 140° C. for 20 minutes. The reaction masses are then combined, poured into water (200 ml) and extracted with AcOEt (2×75 ml). The organic phases are combined, washed with salt water, dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure and the residue crystallizeds from Et2O (25 ml). After recrystallization from EtOH (75 ml), the powder is filtered and dried under vacuum. The expected compound is obtained in the form of a white solid with a yield of 46% (4.1 g). Melting point: 212-213° C.

Workup

  1. customto be placed in a microwave oven
  2. customUnder magnetic stirring, each tube is irradiated at 140° C. for 20 minutes
  3. customThe reaction masses
  4. extractionextracted with AcOEt (2×75 ml)
  5. washwashed with salt water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated under reduced pressure
  9. customthe residue crystallizeds from Et2O (25 ml)
  10. customAfter recrystallization from EtOH (75 ml)
  11. filtrationthe powder is filtered
  12. customdried under vacuum

Sources & evidence

ORD record
ord-910fcfa93bb848e5a3a66e4717dc111f
Source dataset
uspto-grants-2014_01
Patent number
US08624037B2

Reaction notes

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