Dimethylformamide → 2-[1-(4-amino-3-nitrophenyl)ethenyl]-N-[3-(trifluoromethyl)phenyl]benzamide

HRID 2261964Notes

Reaction equation

HRID 2261964 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[O:13])=[CH2:9])=[CH:4][C:3]=1[N+:29]([O-:31])=[O:30].[N-:32]=[N+]=[N-].[Na+].CN(C)C=O.[BH4-].[Na+]>C(OCC)(=O)C.O1CCCC1>[NH2:32][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[O:13])=[CH2:9])=[CH:4][C:3]=1[N+:29]([O-:31])=[O:30]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 4311764Sodium borohydrideHCID 67045429HCID 67045429, compound

Product 1

HCID 670444852-[1-(4-amino-3-nitrophenyl)ethenyl]-N-[3-(trifluoromethyl)phenyl]benzamideYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-[1-(4-chloro-3-nitrophenyl)ethenyl]-N-[3-(trifluoromethyl)phenyl]benzamide (0.72 g, 1.6 mmol), sodium azide (3.1 g, 4.8 mmol) and N,N-dimethylformamide (2 mL) was stirred 60° C. for 18 hours. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (3×30 mL), brine (30 mL), dried over sodium sulfate, filtered and concentrated to give an oily residue. This residue was dissolved in tetrahydrofuran, cooled to 0° C. then sodium borohydride (0.11 g, 2.7 mmol) was added and stirring was continued for 30 minutes at room temperature. The reaction mixture was quenched with methanol (2 mL), concentrated then diluted with ethyl acetate (50 mL). The organic solution was washed with water (30 mL) then brine solution (30 mL) then dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, eluting with 15-50% ethyl acetate-hexane) to give 2-[1-(4-amino-3-nitrophenyl)ethenyl]-N-[3-(trifluoromethyl)phenyl]benzamide (0.35 g, 0.8 mmol, 50% yield). MS (EI) for C22H16F3N3O3: 428 (MH+).

Workup

  1. washwashed with water (3×30 mL), brine (30 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give an oily residue
  6. temperaturecooled to 0° C.
  7. stirringstirring
  8. waitwas continued for 30 minutes at room temperature
  9. customThe reaction mixture was quenched with methanol (2 mL)
  10. concentrationconcentrated
  11. additionthen diluted with ethyl acetate (50 mL)
  12. washThe organic solution was washed with water (30 mL)
  13. dry with materialbrine solution (30 mL) then dried over sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customThe residue was purified by flash chromatography (silica gel, eluting with 15-50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-35e1c3c670434e169dc83b35f4289a1f
Source dataset
uspto-grants-2010_12
Patent number
US07846959B2

Reaction notes

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