Hydrogen Bromide → Ethyl 2-amino-5-(2-bromoacetyl)-4-thiazolecarboxylate

HRID 648571Notes

Reaction equation

HRID 648571 reaction equation
[C:1]([C:4]1[S:8][C:7]([NH2:9])=[N:6][C:5]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2].[BrH:15].Br.[NH+]1C=CC=CC=1.O>C(O)(=O)C>[NH2:9][C:7]1[S:8][C:4]([C:1](=[O:3])[CH2:2][Br:15])=[C:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:6]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 20145082HCID 20145082, compoundHCID 21226041Pyridinium hydrobromide

Product 1

HCID 20145096Ethyl 2-amino-5-(2-bromoacetyl)-4-thiazolecarboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of ethyl 5-acetyl-2-amino-4-thiazolecarboxylate (12.9 g) in a mixture of 30% solution of hydrogen bromide in acetic acid (50 ml) and acetic acid (50 ml) was added pyridinium hydrobromide perbromide (21.1 g) at ambient temperature and stirred for one hour. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was washed with diisopropyl ether to give ethyl 2-amino-5-(2-bromoacetyl)-4-thiazolecarboxylate (14.86 g). mp 164°-166° C. (dec.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-2b095dca9ce44d11a822b52c8ee308cf
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

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