Benzhydrol 2-[2-[3-(octyl) ureido]-4-trifluoromethylphenoxy)benzoate → HCID 15291674, compound

HRID 2399299Notes

Reaction equation

HRID 2399299 reaction equation
C(O)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:15]([NH:23][C:24](=[O:46])[NH:25][C:26]1[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][C:27]=1[O:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31]([O-:33])=[O:32])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>[Pd].C(OCC)(=O)C.C(Cl)(Cl)Cl>[CH2:15]([NH:23][C:24](=[O:46])[NH:25][C:26]1[CH:41]=[C:40]([C:42]([F:44])([F:45])[F:43])[CH:39]=[CH:38][C:27]=1[O:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31]([OH:33])=[O:32])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 1

HCID 131719121Benzhydrol 2-[2-[3-(octyl) ureido]-4-trifluoromethylphenoxy)benzoate

Product 1

HCID 15291674HCID 15291674, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzhydrol 2-[2[3-(octyl)ureido]-4-trifluoromethylphenoxy)-benzoate (290 mg, 0.00047 mol) and 10% palladium on carbon (100 mg) in ethyl acetate was hydrogenated in a parr bottle, at 55 psi for three hours. The mixture was diluted with chloroform, filtered through Celite and the filtrate evaporated. The residue was flash chromatographed (silica gel, ethyl acetate/hexane/formic acid) to give the title compound. 1H NMR (250 MHz, CD3OD) δ8.52 (d, 1H), 7.95 (dd, 1H), 7.6 (tt, 1H), 7.35 (tt, 1H), 7.14 (dd, 2H),6.7 (d, 1H), 3.15 (t, 1H), 1.3 (s, 14H) 0.85 (t, 3H).

Workup

  1. filtrationfiltered through Celite
  2. customthe filtrate evaporated
  3. customchromatographed (silica gel, ethyl acetate/hexane/formic acid)

Sources & evidence

ORD record
ord-f551775c6f094da2b42a1560829e6844
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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