Thioacetamide → 7-bromo-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

HRID 2116665Notes

Reaction equation

HRID 2116665 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13](=O)[CH2:14]Br)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[C:17]([NH2:20])(=[S:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[N:20]=[C:17]([CH3:18])[S:19][CH:14]=3)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 233702397-bromo-4-(bromoacetyl)-2H-chromen-2-one

Product 1

HCID 598148377-bromo-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 7-bromo-4-(bromoacetyl)-2H-chromen-2-one (0.605 g, 1.7 mmol) in DMF was added thioacetamide (0.138 g, 1.8 mmol). The mixture was stirred 24 h at rt and at 100° C. overnight. Once cool to rt, it was partitioned between aqueous NH4Cl and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated and the residue swished in hexanes/Et2O to give the title compound.

Workup

  1. temperatureOnce cool to rt
  2. customit was partitioned between aqueous NH4Cl and EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c33af81955c0450cb8ae90c00e01350a
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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