Sodium Acetate → HCID 20294038, compound

HRID 2163512Notes

Reaction equation

HRID 2163512 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7](Br)[S:8][C:9]=1[CH3:10])(=[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][C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 20294040HCID 20294040, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20294038HCID 20294038, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-acetamido-2-bromo-5-methylthiazole (2.3 g) and sodium acetate (0.8 g) in methanol (60 ml) was hydrogenated at atmospheric pressure over 10% Pd/C catalyst until the theoretical uptake of hydrogen had occurred. The catalyst was removed by filtration and washed with methanol and the filtrate was evaporated to dryness. The residue was extracted with hot CCl4 and the extracts were evaporated. The residue was recrystallised once from petroleum ether (b.p. 60°-80° C.) and once from hexane to give 4-acetamido-5-methylthiazole (0.2 g) m.p. 62°-4° C. (Found: C, 46.6; H, 5.3; N, 18.1. 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 filtrate was evaporated to dryness
  4. extractionThe residue was extracted with hot CCl4
  5. customthe extracts were evaporated
  6. customThe residue was recrystallised once from petroleum ether (b.p. 60°-80° C.) and once from hexane

Sources & evidence

ORD record
ord-4c56de5f3b1648b982ed428b6d919035
Source dataset
uspto-grants-1979_01
Patent number
US04134984

Reaction notes

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