Thioacetamide → 2,6-Difluoro-N-(2'-methyl-5-(3-(trifluoromethyl)phenyl)-4,4'-bithiazol-2-yl)benzamide

HRID 1255143Notes

Reaction equation

HRID 1255143 reaction equation
Br[CH2:2][C:3]([C:5]1[N:6]=[C:7]([NH:20][C:21](=[O:30])[C:22]2[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=2[F:29])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)=O.[C:31](=[S:34])([NH2:33])[CH3:32]>CCO>[F:29][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([F:28])[C:22]=1[C:21]([NH:20][C:7]1[S:8][C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[C:5]([C:3]2[N:33]=[C:31]([CH3:32])[S:34][CH:2]=2)[N:6]=1)=[O:30]

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 24765772N-(4-(2-Bromoacetyl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)-2,6-difluorobenzamide

Product 1

HCID 590044992,6-Difluoro-N-(2'-methyl-5-(3-(trifluoromethyl)phenyl)-4,4'-bithiazol-2-yl)benzamideYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of Compound 85 (51 mg, 0.1 mmol) in 5 mL of EtOH was added ethanethioamide (0.2 mmol) at room temperature. The resulting solution was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the residue was redissolved in ethyl acetate. The solution was treated with saturated solution of NaHCO3 and extracted with ethyl acetate. The combined extracts were dried (Na2SO4) and concentrated. Column chromatography on silica gel (eluted with ethyl acetate) gave Compound 86 (41 mg, 86%) as a yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was redissolved in ethyl acetate
  3. additionThe solution was treated with saturated solution of NaHCO3
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3bcaecc0e66a456aa4628ce457e8d5cd
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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