Acetonitrile → 4-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzoic acid methyl ester

HRID 2103423Notes

Reaction equation

HRID 2103423 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C.Br[CH2:22][C:23]1[S:27][C:26]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)=[N:25][C:24]=1[CH3:38]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:22][C:23]2[S:27][C:26]([C:28]3[CH:29]=[CH:30][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:32][CH:33]=3)=[N:25][C:24]=2[CH3:38])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 27946295-(Bromomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

Product 1

HCID 578043074-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzoic acid methyl esterYield 89.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-hydroxy-benzoic acid methyl ester (152 mg, 1 mmol) and potassium carbonate (152 mg, 1.1 mmol) add acetonitrile (4 mL). To this mixture add 5-bromomethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (Example 4, 314 mg, 1 mmol). Warm the resulting reaction mixture to 60° C., and stir at this temperature for 5 hrs. Cool the mixture to room temperature, dilute with ethyl acetate, wash with water, then brine, dry over MgSO4, filter and concentrate to give the title compound as a white solid (364 mg).

Workup

  1. temperatureWarm
  2. customthe resulting reaction mixture to 60° C.
  3. washwash with water
  4. dry with materialbrine, dry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-4b1b0120916440c5a549d33f529ff27a
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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