Acetic Acid → HCID 20145020, compound

HRID 648572Notes

Reaction equation

HRID 648572 reaction equation
[C:1]([C:4]1[S:8][C:7]([NH:9][CH3:10])=[N:6][C:5]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:3])[CH3:2].C(O)(=O)C.[BrH:20].Br.[NH+]1C=CC=CC=1>O>[Br:20][CH2:2][C:1]([C:4]1[S:8][C:7]([NH:9][CH3:10])=[N:6][C:5]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:3]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 20144967HCID 20144967, compoundHCID 21226041Pyridinium hydrobromide

Product 1

HCID 20145020HCID 20145020, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 5-acetyl-2-methylamino-4-thiazolecarboxylate (7.1 g), 30% acetic acid solution of hydrogen bromide (10 ml) and acetic acid (50 ml) was added pyridinium hydrobromide perbromide (9.9 g) at ambient temperature and stirred for 2.5 hours. The reaction mixture was poured into water (300 ml) and the precipitate was collected by filtration. The precipitate was dissolved in a mixture of ethyl acetate and water and the resultant mixture was adjusted to pH 7.0 with 20% aqueous potassium carbonate. The organic extracted was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was washed with ethyl ether to give ethyl 5-(2-bromoacetyl)-2-methylamino-4-thiazolecarboxylate (6.6 g). mp 130°-131.5° C.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. dissolutionThe precipitate was dissolved in a mixture of ethyl acetate and water
  3. extractionThe organic extracted
  4. washwas washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. washThe residue was washed with ethyl ether

Sources & evidence

ORD record
ord-8731237eee4a49ddae96ac948f5b5f27
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

Loading…