Bromine → HCID 89655859, compound

HRID 930923Notes

Reaction equation

HRID 930923 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8](=[O:11])[NH:9][CH:10]=1)(=[O:4])=[O:3].C([O-])(=O)C.[Na+].[Br:17]Br>C(O)(=O)C>[Br:17][C:7]1[C:8](=[O:11])[NH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=1

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 517045Sodium AcetateHCID 575879665-Methanesulfonyl-1H-pyridin-2-one

Product 1

HCID 89655859HCID 89655859, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of Example 288c (0.671 g, 3.87 mmol) and sodium acetate (0.318 g, 3.87 mmol) in acetic acid (8.50 mL) was added bromine (0.201 mL, 3.91 mmol) dropwise as a solution in acetic acid (1.7 mL). The reaction mixture was stirred at 40° C. for 3 hours. Bromine (0.05 mL) was added, and the reaction mixture was stirred at 40° C. for 2 hours. The reaction mixture was cooled to ambient temperature and quenched with 100 mL of 10% aqueous sodium thiosulfate. The resulting suspension was filtered, and the solid collected and dried for 16 hours to provide the title compound (0.64 g, 66%).

Workup

  1. stirringthe reaction mixture was stirred at 40° C. for 2 hours
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customquenched with 100 mL of 10% aqueous sodium thiosulfate
  4. filtrationThe resulting suspension was filtered
  5. customthe solid collected
  6. customdried for 16 hours

Sources & evidence

ORD record
ord-f14a66215ab945fcb59be10991922590
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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