Pyridine → HCID 20294040, compound

HRID 1413207Notes

Reaction equation

HRID 1413207 reaction equation
Br.[NH2:2][C:3]1[N:4]=[C:5]([Br:9])[S:6][C:7]=1[CH3:8].N1C=CC=CC=1.[C:16]([O-])(=[O:18])[CH3:17].[Na+]>C(OC(=O)C)(=O)C>[C:16]([NH:2][C:3]1[N:4]=[C:5]([Br:9])[S:6][C:7]=1[CH3:8])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 517045Sodium AcetateHCID 20294027HCID 20294027, compound

Product 1

HCID 20294040HCID 20294040, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 4-amino-2-bromo-5-methylthiazole hydrobromide (50 mM, 13.7 g) in acetic anhydride (100 ml) was treated dropwise with pyridine (10 ml) while cooling in an ice bath. After stirring for 1 hour the reaction mixture was poured onto 20% aqueous sodium acetate (1 l) and the aqueous solution extracted with dichloromethane (3×500 ml.). The combined organic layers were dried and evaporated under reduced pressure to give an oil which crystallised on trituration with ether. The crude product was recrystallised from ethanol to give the 4-acetamido-2-bromo-5-methylthiazole (11.7 g, 50%). mp 129°.

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionthe aqueous solution extracted with dichloromethane (3×500 ml.)
  3. customThe combined organic layers were dried
  4. customevaporated under reduced pressure
  5. customto give an oil which
  6. customcrystallised on trituration with ether
  7. customThe crude product was recrystallised from ethanol

Sources & evidence

ORD record
ord-0499512fc2fe4ef7bd6f13c5a43aedad
Source dataset
uspto-grants-1981_02
Patent number
US04249012

Reaction notes

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