Pyridine → HCID 20294040, compound

HRID 26197Notes

Reaction equation

HRID 26197 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 h. the reaction mixture was poured onto 20% aqueous sodium acetate (1l) 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 title compound (11.7 g, 50%). mp 129° (Found: C, 31.15; H, 3.15; N, 12.3. C6H7BrN2OS requires: C, 30.6; H, 3.0; N, 11.9%).

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-2f3e6aff3dbc48a2847a264c4952aaa5
Source dataset
uspto-grants-1979_04
Patent number
US04148904

Reaction notes

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