Sodium Acetate → 4-Propionamidothiazole

HRID 1413211Notes

Reaction equation

HRID 1413211 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([NH:7][C:8](=[O:11])[CH2:9][CH3:10])[N:6]=1.C([O-])(=O)C.[Na+].[H][H]>CO.[Pd]>[C:8]([NH:7][C:5]1[N:6]=[CH:2][S:3][CH:4]=1)(=[O:11])[CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 202940462-Bromo-4-propionamidothiazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 202940354-PropionamidothiazoleYield 71.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-bromo-4-propionamidothiazole (4 g) and sodium acetate (1.4 g) in methanol (100 ml.) was hydrogenated at atmospheric pressure over 10% Pd/C catalyst (1.0 g) until the theoretical uptake of hydrogen and occurred. The catalyst was removed by filtration and washed with methanol and the extracts evaporated in vacuo. The residue was recrystallised twice from carbon tetrachloride to give the title compound (1.9 g) m.p. 129°-32° C. (Found: C, 46.3; H, 5.2; N, 17.7. C6H8N2OS requires C, 46.1; H, 5.2; N, 17.9%).

Workup

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

Sources & evidence

ORD record
ord-645e0b9d75e8451a905a0b69c077c95e
Source dataset
uspto-grants-1981_02
Patent number
US04249012

Reaction notes

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