Methanol → Methyl 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)picolinate

HRID 409713Notes

Reaction equation

HRID 409713 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[NH:10][C:11]2[CH:26]=[CH:25][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([OH:24])=[O:23])[CH:17]=3)=[CH:13][C:12]=2[F:27])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].S(=O)(=O)(O)O.[CH3:38]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[NH:10][C:11]2[CH:26]=[CH:25][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([O:24][CH3:38])=[O:23])[CH:17]=3)=[CH:13][C:12]=2[F:27])=[CH:4][C:3]=1[C:29]([F:31])([F:32])[F:30]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 498422444-(4-(3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)picolinic acid

Product 1

HCID 68248075Methyl 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)picolinateYield 80%

Procedure

4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)picolinic acid (1 g, 2.13 mmol) was suspended in methanol (20 mL). Concentrated sulfuric acid (5 mL) was added at room temperature. The resulted mixture was refluxed for 3 h. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (dichloromethane: methanol=10:1) to give methyl 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)picolinate B8 (0.83 g, purity 97%, yield 80%) as a white solid.

Workup

  1. temperatureThe resulted mixture was refluxed for 3 h
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography (dichloromethane: methanol=10:1)

Sources & evidence

ORD record
ord-380db89ab98c47e7a94e0860685e8c9a
Source dataset
uspto-grants-2014_06
Patent number
US08759531B2

Reaction notes

Loading…