3,5-Bis(trifluoromethyl)phenyl isocyanate → HCID 86748959, compound

HRID 2399290Notes

Reaction equation

HRID 2399290 reaction equation
[CH:1]([OH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][C:17]=1[O:18][C:19]1[CH:27]=[CH:26][C:25]([C:28]([CH3:32])([CH3:31])[CH2:29][CH3:30])=[CH:24][C:20]=1[C:21]([O-:23])=[O:22].[F:41][C:42]([F:57])([F:56])[C:43]1[CH:44]=[C:45]([N:53]=[C:54]=[O:55])[CH:46]=[C:47]([C:49]([F:52])([F:51])[F:50])[CH:48]=1>N1C=CC=CC=1>[CH:1]([OH:14])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:41][C:42]([F:56])([F:57])[C:43]1[CH:44]=[C:45]([NH:53][C:54](=[O:55])[NH:15][C:16]2[CH:36]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:34]=[CH:33][C:17]=2[O:18][C:19]2[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:32])[CH2:29][CH3:30])=[CH:24][C:20]=2[C:21]([O-:23])=[O:22])[CH:46]=[C:47]([C:49]([F:52])([F:50])[F:51])[CH:48]=1

Participants

4

Reactant 2

HCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 86748958HCID 86748958, compound

Product 1

HCID 86748959HCID 86748959, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzhydrol-2-(2-amino-4-trifluoromethylphenoxy)-5-(1,1-dimethylpropyl)benzoate (200 mg, 0.0004 mol) and 3,5-di(trifluoromethyl)phenyl isocyanate (300 μL 0.002 mol) were mixed in pyridine, under argon, at room temperature for 16 h. The solvent was evaporated and the residue flash chromatographed (silica gel, ethyl acetate/hexane) to yield the title compound. 1H NMR (250 MHz, CDCl3) δ8.69 (d, 2H), 7.97 (d, 1H), 7.59 (s, 2H), 7.48 (d, 2H), 7.20-7.39 (m, 9H), 7.08 (d, 1H), 6.95 (s, 1H), 6.82 (dd, 2H), 2.05 (d, 1H), 1.64 (dd, 2H), 1.32 (s, 6H), 0.99 (d, 1H ), 0.72 (t, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue flash chromatographed (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-287e2920c41a49d1817480fa2e8d89f1
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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