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4-(1,1,2,2-tetrafluoroethoxy)aniline → HCID 19779399, compound

HRID 2082038
Notes
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Reaction equation

HRID 2082038 reaction equation
FC(F)(OC1C=CC(N)=CC=1)C(F)F.[F:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([N+:26]([O-])=O)[C:17]=1[N:29]1[C:34](=[O:35])[CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[N:31]=[CH:30]1>C(O)(C)C.O.Cl>[NH2:26][C:18]1[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=[C:16]([F:15])[C:17]=1[N:29]1[C:34](=[O:35])[CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[N:31]=[CH:30]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 27766304-(1,1,2,2-tetrafluoroethoxy)anilineHCID 19779368HCID 19779368, compound

Product 1

HCID 19779399HCID 19779399, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolventHCID 3776
Isopropanol
Solvent

Conditions

Temperature
100 °C

Procedure

4-Nitro-(1',1',2',2'-tetrafluoroethoxy-benzene was converted to 4-(1',1',2',2'-tetrafluoroethoxy)-aniline using the general procedure illustrated in Preparation 12 of EP 0 398 499. In such Preparation, reduced iron powder (0.18 g) was added to a suspension of 1-(2-fluoro-6-nitro-4-trifluoromethylphenyl)-4-trifluoromethylpyrimidin-6-one (0.6 g) in a mixture of isopropanol (6 ml) and water (0.6 ml). Concentrated hydrochloric acid (1 drop) was added, and the reaction mixture was heated to 100° C. for a period of 5 hours. After cooling to ambient temperature, the reaction mixture was filtered through celite, and the residue washed with ethyl acetate. Evaporation of the filtrate under reduced pressure gave 1-(2-amino-6-fluoro-4-trifluoromethylphenyl)-4-trifluoromethylpyrimidin-6-one.

Workup

  1. customillustrated in Preparation 12 of EP 0 398 499
  2. temperatureAfter cooling to ambient temperature
  3. filtrationthe reaction mixture was filtered through celite
  4. washthe residue washed with ethyl acetate
  5. customEvaporation of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-bd01ebcab42a45d8944ddfdd1dd95b83
Source dataset
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05187176

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes