Ethyl Acetate → HCID 59296202, compound

HRID 2233580Notes

Reaction equation

HRID 2233580 reaction equation
F[C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[S:16][C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[N:14][C:13]=2[CH3:27])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C[O-].[Na+].[C:31](OCC)(=[O:33])C>CO>[CH3:31][O:33][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[S:16][C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[N:14][C:13]=2[CH3:27])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 59296174HCID 59296174, compound

Product 1

HCID 59296202HCID 59296202, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

280 mg 2-Fluoro-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-ylmethoxy]-benzonitrile (intermediate example 1) were dissolved in 10 ml methanol. 390 mg sodium methoxide were added and the reaction mixture stirred at a temperature of 60° C. for two hours. The cooled reaction mixture was diluted by adding 200 ml ethyl acetate and washed three times with portions of 50 ml water. The organic layer was dried over MgSO4 and the solvent removed in vacuo to provide 140 mg 2-Methoxy-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile as pale yellow solid.

Workup

  1. customThe cooled reaction mixture
  2. additionwas diluted
  3. washwashed three times with portions of 50 ml water
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-5a1532baf4dd4533af4e93df21f88000
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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