Sodium Acetate → 4-Chloroacetamidothiazole

HRID 1413214Notes

Reaction equation

HRID 1413214 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([NH:7][C:8](=[O:11])[CH2:9][Cl:10])[N:6]=1.C([O-])(=O)C.[Na+].[H][H]>CO.[Pd]>[Cl:10][CH2:9][C:8]([NH:7][C:5]1[N:6]=[CH:2][S:3][CH:4]=1)=[O:11]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 202940332-Bromo-4-chloroacetamidothiazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 202940394-ChloroacetamidothiazoleYield 57.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-bromo-4-chloroacetamidothiazole (4 g) and sodium acetate (1.15 g) in methanol (100 ml) was hydrogenated at atmospheric pressure over 10% Pd/C catalyst (1 g) until theoretical uptake of hydrogen had occurred. The catalyst was removed by filtration and washed with methanol and the extracts evaporated to dryness in vacuo. The residue was recrystallised twice from carbon tetrachloride to give the title compound (1.6 g) m.p. 115°-119° C. (Found: C, 33.7; H, 2.9; N, 15.5. C5H5ClN2OS requires C, 34.0; H, 2.9; N, 15.8%).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. customthe extracts evaporated to dryness in vacuo
  4. customThe residue was recrystallised twice from carbon tetrachloride

Sources & evidence

ORD record
ord-fe2c8561a9974687921e79e9c14c945e
Source dataset
uspto-grants-1981_02
Patent number
US04249012

Reaction notes

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