N-bromobutanimide → HCID 86602191, compound

HRID 349389Notes

Reaction equation

HRID 349389 reaction equation
[CH3:1][C:2]1[S:3](=[C:11]=[O:12])[C:4]([O:8][CH2:9][CH3:10])=[C:5]([OH:7])[N:6]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:1][C:2]1[S:3](=[C:11]=[O:12])[C:4]([O:8][CH2:9][CH3:10])=[C:5]([OH:7])[N:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86602192HCID 86602192, compound

Product 1

HCID 86602191HCID 86602191, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

2-Methyl-5-ethoxy-carbonyl-4-hydroxy-thiazole (45 g, 0.24 mol) was dissolved in 1 L of carbon tetrachloride. The solution was cooled down to 0° C. N-Bromo succinimide (43 g, 0.24 mol) was added portion-wise at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and then warmed to room temperature. The reaction mixture was stirred at room temperature for overnight. The reaction mixture was then passed through a short pad of celite. Removal of solvent gave crude product as solid, which was washed with ethyl acetate/hexane (1/3) three times (1×40 ml; 2×20 ml) to give 30 g of the title compound (yield: 50%; LC: Retention Time=1.66 min; MS: M+1=267).

Workup

  1. temperaturewarmed to room temperature
  2. stirringThe reaction mixture was stirred at room temperature for overnight
  3. customRemoval of solvent
  4. customgave crude product as solid, which
  5. washwas washed with ethyl acetate/hexane (1/3) three times (1×40 ml; 2×20 ml)

Sources & evidence

ORD record
ord-49faa6892202414597b2c375efe0e903
Source dataset
uspto-grants-2007_02
Patent number
US07179827B2

Reaction notes

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