Ethyl Acetate → HCID 23571639, compound

HRID 409335Notes

Reaction equation

HRID 409335 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[S:13])[CH3:12])=[CH:6][CH:5]=1.[OH-].[Na+].CCOC(C)=O>CCO.O>[CH3:12][C:11]1[S:13][C:8]2[CH:9]=[C:4]([O:3][C:2]([F:14])([F:1])[F:15])[CH:5]=[CH:6][C:7]=2[N:10]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86689275HCID 86689275, compound

Product 1

HCID 23571639HCID 23571639, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
90 °C

Procedure

N-(4-(trifluoromethoxy)phenyl)ethanethioamide (38 g, 0.162 mol) was dissolved in EtOH (70 ml), water solution of NaOH (52.5 g, in 175 ml water) was added and the solution was diluted with 350 ml water. This solution was then added drop wise, within 30 min., into a solution of K2Fe(CN)6 (210 g) in 520 ml water at 85-95° C. The reaction mixture was then stirred at 85-95° C. for 1 hr and cooled. TLC (7:3-hexane:EtOAc) was performed. The product was extracted with DCM, the organic phase was dried over Na2SO4, filtered and evaporated and the residue was purified by flash column chromatography (5% EtOAc in hexane) to give 16.8 g (44.5%) of 2-methyl-6-(trifluoromethoxy)benzo[d]thiazole.

Workup

  1. additionThis solution was then added drop wise
  2. customat 85-95° C
  3. temperaturecooled
  4. extractionThe product was extracted with DCM
  5. dry with materialthe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customthe residue was purified by flash column chromatography (5% EtOAc in hexane)

Sources & evidence

ORD record
ord-edb468bb2782428e853a9b82de001c49
Source dataset
uspto-grants-2014_06
Patent number
US08759382B2

Reaction notes

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