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Hydrochloric Acid → 3-(3-Amino-4-trifluoromethoxyphenyl)5,5-dimethyl-1-pyridin-4-ylmethylimidazolidine-2,4-dione

HRID 2356932
Notes
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Reaction equation

HRID 2356932 reaction equation
[CH3:1][C:2]1([CH3:30])[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:5](=[O:14])[N:4]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[C:17]([N+:26]([O-])=O)[CH:16]=2)[C:3]1=[O:29].Cl>O.[Zn]>[NH2:26][C:17]1[CH:16]=[C:15]([N:4]2[C:3](=[O:29])[C:2]([CH3:30])([CH3:1])[N:6]([CH2:7][C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)[C:5]2=[O:14])[CH:20]=[CH:19][C:18]=1[O:21][C:22]([F:23])([F:24])[F:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23110306HCID 23110306, compound

Product 1

HCID 231103083-(3-Amino-4-trifluoromethoxyphenyl)5,5-dimethyl-1-pyridin-4-ylmethylimidazolidine-2,4-dioneYield 57.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

8.8 g (20.7 mmol ) 5,5-dimethyl-3-(3-nitro-4-trifluormethoxy-phenyl)-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione were dissolved in 200 ml semi-conc. hydrochloric acid. 30 g zinc dust were added in portions and the resulting mixture was refluxed for 1 h, cooled to RT, diluted with 100 ml water and extracted with ethyl acetate. The aqueous phase was made alkaline with saturated sodium hydroxide solution and extracted with methylene chloride. Separating zinc salts were removed by filtration over cellite. Evaporation of the combined organic phases and flash chromoatography of the residue (Silica gel, methylene chloride:methanol=95:5) gave 4.7 g of the desired product.

Workup

  1. temperaturethe resulting mixture was refluxed for 1 h
  2. extractionextracted with ethyl acetate
  3. extractionextracted with methylene chloride
  4. customSeparating zinc salts were removed by filtration over cellite
  5. customEvaporation of the combined organic phases and flash chromoatography of the residue (Silica gel, methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-7f2072eb7b7742a695baf08a0bdc93a4
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07759379B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes