Benzhydrol 2-[2-[3-(4-bromophenyl)ureido]-4-(trifluoromethyl)-phenoxy]benzoate → HCID 15291672, compound

HRID 2399276Notes

Reaction equation

HRID 2399276 reaction equation
C(O)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:45])[NH:24][C:25]2[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[CH:37][C:26]=2[O:27][C:28]2[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=2[C:30]([O-:32])=[O:31])=[CH:18][CH:17]=1>C(OCC)(=O)C.[Pd]>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:45])[NH:24][C:25]2[CH:40]=[C:39]([C:41]([F:43])([F:44])[F:42])[CH:38]=[CH:37][C:26]=2[O:27][C:28]2[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=2[C:30]([OH:32])=[O:31])=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 131719120Benzhydrol 2-[2-[3-(4-bromophenyl)ureido]-4-(trifluoromethyl)-phenoxy]benzoate

Product 1

HCID 15291672HCID 15291672, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzhydrol 2-[2-[3-(4-bromophenyl)ureido]-4-(trifluoromethyl)-phenoxy]benzoate (3.7 g, 5 mmol) was dissolved in ethyl acetate (125 mL) and was hydrogenated for 0.75 hour at 50 psi over 10% palladium on carbon (0.5 g). The catalyst was filtered off and the solvent evaporated to give the crude product which was purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid). Recrystallization from ethyl acetate/hexane gave the title compound as a white crystalline solid; mp 229°-231° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated
  3. customto give the crude product which
  4. customwas purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid)
  5. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-233f763480b748338074592c378b5a8b
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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