Acetic Anhydride → 2-Acetamido-5-bromo-1,3-thiazole

HRID 2085364Notes

Reaction equation

HRID 2085364 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1.[C:8](OC(=O)C)(=[O:10])[CH3:9]>C(Cl)Cl.N1C=CC=CC=1>[C:8]([NH:1][C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 436002-Thiazolamine, 5-bromo-

Product 1

HCID 3502602-Acetamido-5-bromo-1,3-thiazole

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-5-bromothiazole (22.3 g, 85.9 mmol) in methylene chloride (100 mL) and pyridine (60 mL) was added acetic anhydride (11 mL) slowly with stirring. The mixture was allowed to stir for 2.5 hours, warmed to room temperature, and stirred for an additional 4 hours. Most of the solvent was removed in vacuo and the residue was washed with ethyl acetate and aqueous HCl. The organic solution was then washed with water, dried over MgSO4 and concentrated to give a crude solid. This solid was triturated with Et2O, filtered, washed with Et2O, and dried to give 2-acetamido-5-bromothiazole as a solid (15.1 g, 80%, C5H5BrN2OS, MS m/e 222 (M+H)+).

Workup

  1. stirringto stir for 2.5 hours
  2. stirringstirred for an additional 4 hours
  3. customMost of the solvent was removed in vacuo
  4. washthe residue was washed with ethyl acetate and aqueous HCl
  5. washThe organic solution was then washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto give a crude solid
  9. customThis solid was triturated with Et2O
  10. filtrationfiltered
  11. washwashed with Et2O
  12. customdried

Sources & evidence

ORD record
ord-fa634bd407bb4c199cbf06909d1817ec
Source dataset
uspto-grants-2004_04
Patent number
US06720347B2

Reaction notes

Loading…