Pyridine → 4-Acetamido-2-bromo-thiazole

HRID 26195Notes

Reaction equation

HRID 26195 reaction equation
Br.[NH2:2][C:3]1[N:4]=[C:5]([Br:8])[S:6][CH:7]=1.N1C=CC=CC=1.[C:15]([O-])(=[O:17])[CH3:16].[Na+]>C(OC(=O)C)(=O)C>[C:15]([NH:2][C:3]1[N:4]=[C:5]([Br:8])[S:6][CH:7]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 517045Sodium AcetateHCID 202940412-Bromo-1,3-thiazol-4-amine--hydrogen bromide (1/1)

Product 1

HCID 202940434-Acetamido-2-bromo-thiazoleYield 80%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-2-bromothiazole hydrobromide (52 g, 0.2 m) was suspended in acetic anhydride (200 ml) then treated dropwise with pyridine (100 ml), maintaining the temperature at 0° C. by means of an ice bath. After the addition was complete, the reaction mixture was stirred for 2 h. at room temperature then poured onto 20% aqueous sodium acetate (2 l). The solution was cooled, filtered and the precipitate washed with water (2×200 ml.). The product was air dried and recrystallised from acetone to give the title compound (35 g, 80%). m.p. 165° C. Found: C, 27.5; H, 2.5; N, 12.7. C5H5BrN2OS requires C, 27.2; H, 2.3; N, 12.7%.

Workup

  1. additionAfter the addition
  2. temperatureThe solution was cooled
  3. filtrationfiltered
  4. washthe precipitate washed with water (2×200 ml.)
  5. customdried
  6. customrecrystallised from acetone

Sources & evidence

ORD record
ord-1b27dabd453244c981454e92d07e796b
Source dataset
uspto-grants-1979_04
Patent number
US04148904

Reaction notes

Loading…