Thiobenzamide → 2-Phenyl-4-(pyridin-4-yl)thiazole

HRID 538423Notes

Reaction equation

HRID 538423 reaction equation
Br.Br[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=O.[C:12]([NH2:20])(=[S:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[C:13]1([C:12]2[S:19][CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=3)[N:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 683563ThiobenzamideHCID 27762394-(Bromoacetyl)pyridine hydrobromide

Product 1

HCID 665911812-Phenyl-4-(pyridin-4-yl)thiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 4-(bromoacetyl)pyridine hydrobromide (500 mg, 1.8 mmol) in dry DMF (5 mL) was added thiobenzamide (242 mg, 1.8 mmol,) and the resulting reaction was stirred at rt for 12 h. Thereafter, the reaction quenched with saturated aqueous NaHCO3 solution (25 mL) and the mixture extracted with EtOAc (3×25 mL). The combined organic extracts were washed with water (25 mL), dried (Na2SO4), and concentrated. The resulting residue was purified by flash chromatography (SiO2, 100:0-0:100 hexanes-EtOAc) furnished 2-phenyl-4-(pyridin-4-yl)thiazole: LCMS (m/z): 239.0 (MH+), tR=0.64 min.

Workup

  1. customthe resulting reaction
  2. customThereafter, the reaction quenched with saturated aqueous NaHCO3 solution (25 mL)
  3. extractionthe mixture extracted with EtOAc (3×25 mL)
  4. washThe combined organic extracts were washed with water (25 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (SiO2, 100:0-0:100 hexanes-EtOAc)

Sources & evidence

ORD record
ord-7595047a5dba45c5b9a0c8e1a33716fe
Source dataset
uspto-grants-2014_10
Patent number
US08865732B2

Reaction notes

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