4-Aminophenol → N-[4-Chloro-3-(trifluoromethyl)phenyl]-N'-(4-hydroxyphenyl)urea
Reaction equation
ClC(Cl)(Cl)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:7]=1)=[O:4].N12CCCN=C1CCCCC2.[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1>CN(C)C=O.C(#N)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)=[O:4])=[CH:7][C:8]=1[C:13]([F:16])([F:15])[F:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 115 °C
Procedure
2,2,2-trichloro-N-(4-chloro-3-(trifluoromethyl)phenyl)acetamide (25 g, 0.07338 mol) was dissolved in dimethyl formamide (75 ml). 1,8-diazabicyclo[5.4.0]undec-7-ene (17.5 ml, 0.11731 mol) and 4-amino phenol (9.6 g, 0.0879 mol) were added in one lot. The reaction mass was heated to 110-120° C. for 18-20 hours, cooled to room temperature and quenched in water (750 ml). The quenched mass was extracted repeatedly with ethyl acetate and the combined ethyl acetate layer was then back washed with water. It was then dried over sodium sulfate and evaporated under vacuum to obtain solid. The obtained solid was slurried in acetonitrile (300 ml) at ambient temperature and filtered to give 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(4-hydroxyphenyl)urea (18 g).
Workup
- temperaturecooled to room temperature
- customquenched in water (750 ml)
- extractionThe quenched mass was extracted repeatedly with ethyl acetate
- washthe combined ethyl acetate layer was then back washed with water
- dry with materialIt was then dried over sodium sulfate
- customevaporated under vacuum
- customto obtain solid
- filtrationfiltered
Sources & evidence
- ORD record
- ord-a9c525ee60db4ce98914c94bf921fd87
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445687B2
Reaction notes
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