HCID 18995948, compound → 4-Amino-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

HRID 37578Notes

Reaction equation

HRID 37578 reaction equation
[N+:1]([C:4]1[C:12]2[O:11][C:10]([CH:17]([Cl:22])[C:18]([F:21])([F:20])[F:19])([C:13]([F:16])([F:15])[F:14])[O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.[H][H].[Pd]>[NH2:1][C:4]1[C:12]2[O:11][C:10]([CH:17]([Cl:22])[C:18]([F:21])([F:19])[F:20])([C:13]([F:14])([F:15])[F:16])[O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 18995948HCID 18995948, compound

Product 1

HCID 189959374-Amino-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

84 g of 4-nitro-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole from Example 7 were dissolved in 500 ml of tetrahydrofuran and hydrogenated with 15-20 bar of hydrogen for 5 hours at room temperature on 5 g of palladium-on-charcoal (5%). The mixture was then filtered and the filtrate was concentrated and distilled under vacuum. The yield was 31 g (40% of theory) and the boiling point was 70° C. at 0.1 mbar. The NMR spectra showed the following characteristic absorptions: 19F NMR: -68.6 and -81.5 ppm. 1H NMR: 4.69 ppm.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated
  3. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-590ec5b6d1af4457b7e7130097e67a87
Source dataset
uspto-grants-1995_05
Patent number
US05420309

Reaction notes

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