Pyridine → 4-Acrylamido-2-bromothiazole

HRID 26200Notes

Reaction equation

HRID 26200 reaction equation
Br.[NH2:2][C:3]1[N:4]=[C:5]([Br:8])[S:6][CH:7]=1.[C:9](Cl)(=[O:12])[CH:10]=[CH2:11].N1C=CC=CC=1.C([O-])(=O)C.[Na+]>C(Cl)Cl>[C:9]([NH:2][C:3]1[N:4]=[C:5]([Br:8])[S:6][CH:7]=1)(=[O:12])[CH:10]=[CH2:11]

Participants

6

Reactant 4

HCID 1049PyridineHCID 13140Acryloyl chlorideHCID 517045Sodium AcetateHCID 202940412-Bromo-1,3-thiazol-4-amine--hydrogen bromide (1/1)

Product 1

HCID 203771664-Acrylamido-2-bromothiazoleYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-2-bromothiazole hydrobromide (15.6 g) and acryloylchloride (7 g) were suspended in methylene chloride (100 ml) with stirring and treated with pyridine (16 ml), maintaining reaction temperature at 0° C. with an ice bath. After addition was complete, the reaction mixture was stirred at room temperature for 3 hours, then poured onto 20% aqueous sodium acetate and stirred for 30 minutes. The mixture was filtered and separated and the organic layer washed with 2N hydrochloric acid, water, sodium carbonate solution and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo. The residue was recrystallised from carbon tetrachloride to give the title compound (0.7 g) m.p. 152°-4° C. (Found: C, 30.5; H, 2.2; N, 11.8. C6H5BrN2OS requires C, 30.9; H, 2.2; N, 12.0%).

Workup

  1. temperaturemaintaining
  2. customreaction temperature at 0° C. with an ice bath
  3. additionAfter addition
  4. stirringthe reaction mixture was stirred at room temperature for 3 hours
  5. stirringstirred for 30 minutes
  6. filtrationThe mixture was filtered
  7. customseparated
  8. washthe organic layer washed with 2N hydrochloric acid, water, sodium carbonate solution and water
  9. dry with materialThe organic layer was dried (MgSO4)
  10. customthe solvent removed in vacuo
  11. customThe residue was recrystallised from carbon tetrachloride

Sources & evidence

ORD record
ord-d8755e1fbd9044349ba066d6c16f73c2
Source dataset
uspto-grants-1979_04
Patent number
US04148904

Reaction notes

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