Sodium Acetate → HCID 19385671, compound

HRID 1413213Notes

Reaction equation

HRID 1413213 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([NH:7][C:8](=[O:12])[CH2:9][CH2:10][CH3:11])[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:12])[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 20294032HCID 20294032, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19385671HCID 19385671, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-bromo-4-butyramidothiazole (4 g) and sodium acetate (1.35 g) in methanol (100 ml) was hydrogenated at atmospheric pressure over 10% Pd/C (1 g) as catalyst until theoretical uptake of hydrogen had occurred. The catalyst was removed by filtration and washed with methanol and the extracts evaporated in vacuo. The residue was recrystallised from hexane and the crystals sublimed at 50° C. at 0.2 mm and the sublimate recrystallised from carbon tetrachloride to give the title compound (1.1 g) m.p. 63°-6° C. (Found: C, 49.0; H, 5.9; N, 16.5. C7H10N2OS requires C, 49.4; H, 5.9; N, 16.5%).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. customthe extracts evaporated in vacuo
  4. customThe residue was recrystallised from hexane
  5. customsublimed at 50° C. at 0.2 mm
  6. customthe sublimate recrystallised from carbon tetrachloride

Sources & evidence

ORD record
ord-9f1f9312fa1b4755b67051653188e49d
Source dataset
uspto-grants-1981_02
Patent number
US04249012

Reaction notes

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