Hydrochloric Acid → Ethyl 2-(2-bromo-1,3-thiazol-4-yl)acetate

HRID 546879Notes

Reaction equation

HRID 546879 reaction equation
N([O-])=O.[Na+].[CH2:5]([O:7][C:8](=[O:16])[CH2:9][C:10]1[N:11]=[C:12](N)[S:13][CH:14]=1)[CH3:6].[Br-:17].[Na+].Cl>O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:5]([O:7][C:8](=[O:16])[CH2:9][C:10]1[N:11]=[C:12]([Br:17])[S:13][CH:14]=1)[CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 253881Sodium BromideHCID 23668193Sodium Nitrite

Product 1

HCID 53428667Ethyl 2-(2-bromo-1,3-thiazol-4-yl)acetateYield 6%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (1.18 g, 0.0171 mol) in water (10 mL) was added dropwise to a mixture of (2-amino-thiazol-4-yl)acetic acid ethyl ester (2.60 g, 0.0140 mol), copper sulfate (6.84 g, 0.0429 mol), sodium bromide (5.89 g, 0.0573 mol) and 9 M hydrochloric acid aqueous solution (30 mL) at 0° C. over 10 minutes. After stirring at the same temperature for 20 minutes, the reaction solution was returned to room temperature over one hour and further stirred at room temperature for two hours. The reaction solution was diluted with water, filtered through celite and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography (n-hexane/ethyl acetate=1/0 to 9/1) to give the title compound (209.3 mg, 6%).

Workup

  1. waitthe reaction solution was returned to room temperature over one hour
  2. stirringfurther stirred at room temperature for two hours
  3. filtrationfiltered through celite
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-444d028b37cb4b77b1e030923c2190b2
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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