Acetic Acid → HCID 20145020, compound

HRID 1905991Notes

Reaction equation

HRID 1905991 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 extract 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 extract
  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-fb2a9557887d4c24b6909fe6de2fffe3
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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