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

HRID 1988213Notes

Reaction equation

HRID 1988213 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 is added thioacetamide (0.138 g, 1.8 mmol). The mixture is stirred 24 h at rt and at 100° C. overnight. Once cool to rt, it is partitioned between aqueous NH4Cl and EtOAc. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic layers are washed with brine and dried over anhydrous Na2SO4. The solvent is evaporated and the residue swished in hexanes/Et2O to give the title compound.

Workup

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

Sources & evidence

ORD record
ord-ab26fd90653f4774805dbe4a8147a319
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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