2-Methoxy-5-(trifluoromethyl)aniline → 3-(4-Aminophenoxy)benzoic acid

HRID 78358

Reaction equation

HRID 78358 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([O:10][CH3:11])=[C:7]([CH:9]=1)[NH2:8].FC(F)(F)C1C=CC(OC)=C([N:22]=[C:23]=[O:24])C=1.[C:29]([C:32]1[CH:33]=[C:34]([CH:43]=[CH:44][CH:45]=1)[O:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1)([OH:31])=[O:30]>>[C:29]([C:32]1[CH:33]=[C:34]([CH:43]=[CH:44][CH:45]=1)[O:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1)([OH:31])=[O:30].[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([O:10][CH3:11])=[C:7]([NH:8][C:23]([NH:22][C:34]2[CH:43]=[CH:44][CH:45]=[C:32]([C:29]([OH:31])=[O:30])[CH:33]=2)=[O:24])[CH:9]=1

Participants

5

Reactant 3

HCID 6006372-Methoxy-5-(trifluoromethyl)anilineHCID 11983909Benzene, 2-isocyanato-1-methoxy-4-(trifluoromethyl)-2×HCID 230090363-(4-Aminophenoxy)benzoic acid

Product 2

HCID 230090363-(4-Aminophenoxy)benzoic acidHCID 23614600N-(5-(trifluoromethyl)-2-methoxyphenyl)-N'-(3-carboxyphenyl)urea

Procedure

Entry 39: 4-(3-Carboxyphenoxy)aniline was synthesized according to Method A11. 5-(Trifluoromethyl)-2-methoxyaniline was converted into 5-(trifluoromethyl)-2-methoxyphenyl isocyanate according to Method B1. 4-(3-Carboxyphenoxy)aniline was reacted with 5-(trifluoromethyl)-2-methoxyphenyl isocyanate according to Method C1f to afford N-(5-(trifluoromethyl)-2-methoxyphenyl)-N′-(3-carboxyphenyl)urea, which was coupled with 4-morpholinoaniline according to Method D1c.

Sources & evidence

ORD record
ord-38f42cd5c9cf4714bf58274e66373df2
Source dataset
uspto-grants-2014_09
Patent number
US08841330B2

Linked notes

Loading…