Sodium Acetate → 4-Acetamidothiazole

HRID 1413206Notes

Reaction equation

HRID 1413206 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7](Br)[S:8][CH:9]=1)(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].[H][H]>CO.[Pd]>[C:1]([NH:4][C:5]1[N:6]=[CH:7][S:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 202940434-Acetamido-2-bromo-thiazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 202940374-AcetamidothiazoleYield 84.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-acetamido-2-bromo-thiazole (22 g., 0.2 m) and sodium acetate (8.2 g, 0.1 m) in methanol (600 ml) was hydrogenated at room temperature and 1 atm. pressure oven 10% palladium on carbon (5 g) until the theoretical uptake of hydrogen had occurred (about 3 hours). The catalyst was removed by filtration and the filtrate evaporated to dryness under reduced pressure. The residue was extracted with carbon tetrachloride (200 ml) in a Soxlet apparatus. The extract was cooled and the crystals removed by filtration to yield 4-acetamidothiazole (12 g, 78%). m.p. 176° C. Found: C, 41.8; H, 4.3; N, 19.3. C5H6N2OS requires: C, 42.2; H, 4.3; N, 19.7%.

Workup

  1. customwas hydrogenated at room temperature
  2. custom(about 3 hours)
  3. customThe catalyst was removed by filtration
  4. customthe filtrate evaporated to dryness under reduced pressure
  5. extractionThe residue was extracted with carbon tetrachloride (200 ml) in a Soxlet apparatus
  6. temperatureThe extract was cooled
  7. customthe crystals removed by filtration

Sources & evidence

ORD record
ord-ea92f29ea8794b19b3f1042fc68f7cfc
Source dataset
uspto-grants-1981_02
Patent number
US04249012

Reaction notes

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