Phenyl isocyanate → N-[3,5-Bis(trifluoromethyl)phenyl]-2-hydroxy-5-[(3-phenyl)ureido]benzamide

HRID 2384386Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1)=[O:8].[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C.CN(C)C1C=CN=CC=1>[F:23][C:20]([F:21])([F:22])[C:12]1[CH:11]=[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:24]=[C:2]([NH:1][C:33]([NH:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:34])[CH:3]=[CH:4][C:5]=2[OH:25])[CH:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

5-Amino-N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxybenzamide (100.2 mg, 0.28 mmol) was dissolved in acetonitrile (4 ml). 4-Dimethylaminopyridine (3 mg) and phenylisocyanate (30 μl, 0.28 mmol) were added, and the mixture was stirred at 60° C. for 5 minutes. The reaction mixture was concentrated and the residue was purified by chromatography on silica gel (hexane:ethyl acetate=1:1) to give the title compound (54.8 mg, 41.2%) as a light brown solid.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-74a5f5335e394df790e4abbe5eccbcc3
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263657B2

Reaction notes

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