Hydrogen Bromide → Methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate

HRID 1816627Notes

Reaction equation

HRID 1816627 reaction equation
N[C:2]1[S:3][C:4]([CH3:11])=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.N([O-])=O.[Na+].O.[BrH:17]>CO>[Br:17][C:2]1[S:3][C:4]([CH3:11])=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1

Participants

6

Reactant 4

HCID 260Hydrogen Bromide2×HCID 962WaterHCID 1132801Methyl 2-amino-5-methyl-1,3-thiazole-4-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 22493969Methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.8 g of methyl 2-amino-5-methyl-1,3-thiazole-4-carboxylate was dissolved in 30 ml methanol and 7 ml hydrobromic acid, followed by adding dropwise an aqueous solution of 1.2 g sodium nitrite thereinto under ice-cooling. After stirring the reaction solution under ice-cooling for 30 minutes, a solution, previously heated at 60° C., of 1.3 g cuprous bromide in 7 ml hydrobromic acid was added thereto, followed by stirring at 60° C. for 1 hour. The reaction solution was ice-cooled and water was-added, followed by extracting with diethyl ether. The organic layer was extracted with brine, dried over anhydrous magnesium sulfate and evaporated, to give 0.47 g of methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling for 30 minutes
  3. additionwas added
  4. stirringby stirring at 60° C. for 1 hour
  5. temperaturecooled
  6. extractionby extracting with diethyl ether
  7. extractionThe organic layer was extracted with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-0973afc936bb49e184fa255589599e6a
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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