Acetonitrile → 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

HRID 424847Notes

Reaction equation

HRID 424847 reaction equation
BrC[C:3]1[N:7]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:15])[N:6]=[N:5][C:4]=1[C:16]([F:19])([F:18])[F:17].O[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][CH2:29][C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[C:32]([CH3:40])[CH:31]=2)=[C:23](C)[CH:22]=1.[C:42](=[O:45])([O-])[O-].[K+].[K+].[C:48](#N)C>>[CH3:37][O:36][C:34](=[O:35])[C:33]1[CH:38]=[CH:39][C:30]([CH2:29][N:28]([C:27]2[CH:22]=[CH:21][C:26]([O:45][CH2:42][C:3]3[N:7]([C:8]4[C:9]([Cl:15])=[CH:10][CH:11]=[CH:12][C:13]=4[Cl:14])[N:6]=[N:5][C:4]=3[C:16]([F:18])([F:17])[F:19])=[CH:25][C:24]=2[CH3:23])[CH3:48])=[CH:31][C:32]=1[CH3:40]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 667042144-{[(4-Hydroxy-2-methylphenyl)methylamino]methyl}-2-methyl benzoic acid, methyl esterHCID 866292535-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazole

Product 1

HCID 667042114-[({4-[3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methylphenyl}-methylamino)-methyl]-2-methyl-benzoic acid methyl esterYield 97%

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazole (15.65 g, 41.7 mmol) and 4-{[(4-hydroxy-2-methylphenyl)methylamino]methyl}-2-methyl benzoic acid, methyl ester (12.49 g, 41.7 mmol) in acetonitrile (120 mL) is added potassium carbonate (11.54 g, 83.4 mmol) at room temperature. The mixture is heated at 90° C. overnight. After 16 h, the reaction is cooled to room temperature and filtered through a pad of diatomaceous earth. The solvent is removed under reduced pressure. The residue is diluted with MTBE and washed with 2N NaOH, water, and brine. The organic layer is dried over magnesium sulfate, filtered, and evaporated to afford 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, 97%). ES/MS m/e 593 (M+1).

Workup

  1. temperaturethe reaction is cooled to room temperature
  2. filtrationfiltered through a pad of diatomaceous earth
  3. customThe solvent is removed under reduced pressure
  4. additionThe residue is diluted with MTBE
  5. washwashed with 2N NaOH, water, and brine
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-56d5636957a0466dba4866b95eba94c6
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

Loading…