HCID 66968527, compound → HCID 57824514, compound

HRID 1424733Notes

Reaction equation

HRID 1424733 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[C:11]2=[O:26])=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][N:12]([C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]([F:24])([F:25])[F:23])=[CH:19][CH:20]=3)[C:11]2=[O:26])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 66968527HCID 66968527, compound

Product 1

HCID 57824514HCID 57824514, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(4-nitrophenyl)-3-(4-trifluoromethoxyphenyl)-1,3-dihydroimidazol-2-one (144 mg, 0.395 mmol) in EtOH (40 mL) was added 10% Pd/C (100 mg). The mixture was evacuated and flushed with nitrogen three times. The Parr vessel was pressurized to 45 psi of hydrogen and shaken for 5 h. The depressurized solution was filtered through a pad of Celite® and the pad was washed with EtOH (25 mL). The ethanol was removed under reduced pressure to afford the title product (114 mg, 95%): 1H NMR (400 MHz, CDCl3) δ 7.61 (d, J=9.2 Hz, 2H), 7.33 (d, J=9.2 Hz, 2H), 7.21 (d, J=8.6 Hz, 2H), 6.71 (d, J=9.2 Hz, 2H), 3.92 (s, 4H), 3.61 (br s, 2H); EIMS m/z 307 (M+).

Workup

  1. customThe mixture was evacuated
  2. customflushed with nitrogen three times
  3. filtrationThe depressurized solution was filtered through a pad of Celite®
  4. washthe pad was washed with EtOH (25 mL)
  5. customThe ethanol was removed under reduced pressure

Sources & evidence

ORD record
ord-2e326709396c45898f96ce2c6b054cba
Source dataset
uspto-grants-2015_01
Patent number
US08927729B2

Reaction notes

Loading…