Potassium Hydroxide → 4-[({4-[3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methylphenyl}-methylamino)-methyl]-2-methyl-benzoic Acid

HRID 424848Notes

Reaction equation

HRID 424848 reaction equation
C[O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[N:22]([C:30]4[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:37])[N:23]=[N:24][C:25]=3[C:26]([F:29])([F:28])[F:27])=[CH:15][C:14]=2[CH3:38])[CH3:12])=[CH:6][C:5]=1[CH3:39].[OH-].[K+]>CO.C1COCC1>[Cl:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:37])[C:30]=1[N:22]1[C:21]([CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([N:11]([CH2:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:40])=[O:2])=[C:5]([CH3:39])[CH:6]=3)[CH3:12])=[C:14]([CH3:38])[CH:15]=2)=[C:25]([C:26]([F:28])([F:29])[F:27])[N:24]=[N:23]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 667042114-[({4-[3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methylphenyl}-methylamino)-methyl]-2-methyl-benzoic acid methyl ester

Product 1

HCID 248627414-[({4-[3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methylphenyl}-methylamino)-methyl]-2-methyl-benzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[({4-[3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methylphenyl}-methylamino)-methyl]-2-methyl-benzoic acid methyl ester (24.2 g, 40.7 mmol) in MeOH (150 mL) and THF (150 mL) is added 2N potassium hydroxide (102 mL, 203 mmol). The mixture is heated at 60° C. for 2 hours. The solvent is removed under reduced pressure. The residue is diluted with water, acidified to pH 3 with 2N HCl, and extracted with dichloromethane. The organic layer is dried over magnesium sulfate, filtered, and evaporated under reduced pressure to afford the title compound as a white solid that is crystallized from MeOH (20 g, 80%). ES/MS m/e 579 (M+1).

Workup

  1. customThe solvent is removed under reduced pressure
  2. additionThe residue is diluted with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8a4c3676e7e74bb2a9bd24cddcaad21a
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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