Octyl isocyanate → Benzhydrol 2-[2-[3-(octyl) ureido]-4-trifluoromethylphenoxy)benzoate

HRID 2399298Notes

Reaction equation

HRID 2399298 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:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:17]=1[O:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([O-:23])=[O:22].[CH2:36]([N:44]=[C:45]=[O:46])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>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.[CH2:36]([NH:44][C:45](=[O:46])[NH:15][C:16]1[CH:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=[CH:28][C:17]=1[O:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([O-:23])=[O:22])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

4

Reactant 2

HCID 76616Octyl isocyanateHCID 131719119Benzhydrol 2-(2-amino-4-trifluoromethylphenoxy)benzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzhydrol 2-(2-amino-4-trifluoromethylphenoxy)benzoate (700 mg, 0.0015 mol) was dissolved in pyridine and octylisocyanate (412 mg, 0.0027 mol) was added to the mixture at room temperature and stirred for three hours. The solvent was evaporated and the residue was flash chromatographed (silica gel, ethyl acetate/hexane) to give the title compound. 1H NMR (250 MHz, CDCl3) δ8.7 (s, 1H), 8.2 (s, 1H), 7.95 (d, 1H), 7.29 (m, 10H), 7.12 (s, 1H), 7.1 (d, 1H), 7.0 (s, 1H), 6.9 (d, 1H), 4.8 (s, 1H), 3.1 (dd, 1H), 1.28 (s, 14H), 0.85 (t, 3H).

Workup

  1. customThe solvent was evaporated
  2. customchromatographed (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9c438e17448644be9550f2e893b85329
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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