Bromine → 2-Bromo-1-(4-methyl-1,2,3-thiadiazol-5-yl)ethanone

HRID 396538Notes

Reaction equation

HRID 396538 reaction equation
[C:1]([C:4]1[S:8][N:7]=[N:6][C:5]=1[CH3:9])(=[O:3])[CH3:2].[Br:10]Br.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:10][CH2:2][C:1]([C:4]1[S:8][N:7]=[N:6][C:5]=1[CH3:9])=[O:3]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 23003518Ethanone, 1-(4-methyl-1,2,3-thiadiazol-5-yl)- (9CI)

Product 1

HCID 230034502-Bromo-1-(4-methyl-1,2,3-thiadiazol-5-yl)ethanoneYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 5-acetyl-4-methyl-1,2,3-thiadiazole (1.00 g, 7.03 mmol) in chloroform (20 ml) was added dropwise a solution of bromine (1.24 g, 7.73 mmol) in chloroform (10 ml) over 0.5 h at room temperature. The mixture was heated at reflux temperature for 2 h. After cooling to room temperature, the mixture was made basic with saturated aqueous sodium bicarbonate and extracted with dichloromethane (100 ml×2). The extracts were dried (Na2SO4) and concentrated to give 1.55 g (100%) of the title compound as a brown oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 2 h
  3. extractionextracted with dichloromethane (100 ml×2)
  4. dry with materialThe extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-63653b3f43394fddb0f1ab2e4fdaf48a
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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