Reaction #1340588

ord-4ed8b6231e6b40bbb1e175a4a6e4f7a1

Reaction equation

CCc1cc(C(F)(C(F)(F)F)C(F)(F)F)cc(CC)c1NC(=O)c1ccc(-n2cncn2)c([N+](=O)[O-])c1
N-[2,6-diethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethylethyl)phenyl]-3-nitro-4-(1,2,4-triazol-1-yl)benzamide
CCc1cc(C(F)(C(F)(F)F)C(F)(F)F)cc(CC)c1NC(=O)c1ccc(-n2cncn2)c(N)c1
3-amino-N-[2,6-diethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethylethyl)phenyl]-4-(1,2,4-triazol-1-yl)benzamide
Yield 74.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe reaction mixture was filtered
  2. 2
    Concentrationthe filtrate was concentrated
  3. 3
    OtherThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:4)
  4. 4
    Otherto give Compound No

Procedure

A solution of N-[2,6-diethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethylethyl)phenyl]-3-nitro-4-(1,2,4-triazol-1-yl)benzamide (473 mg, 0.89 mmol) (Example I2) in ethanol (9 ml) was charged with palladium on carbon (10%) (140 mg, 0.13 mmol) and was stirred under a atmosphere of hydrogen for 15 hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:4) to give Compound No. B2 of Table B (328 mg, 74% yield) and Compound No. C1 of Table C (18 mg, 4% yield).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08455399B2uspto-grants-2013_06