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

HRID 2082038Notes

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

Participants

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

customillustrated in Preparation 12 of EP 0 398 499
temperatureAfter cooling to ambient temperature
filtrationthe reaction mixture was filtered through celite
washthe residue washed with ethyl acetate
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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