Benzoic Acid → 2-Bromoimidazo[5,1-b]thiazole

HRID 1444174Notes

Reaction equation

HRID 1444174 reaction equation
[Br:1][C:2]1[S:6][C:5]2=[C:7](C(O)=O)[N:8]=[CH:9][N:4]2[CH:3]=1.C(O)(=O)C1C=CC=CC=1>ClC1C=CC(Cl)=CC=1Cl.CCCCCC>[Br:1][C:2]1[S:6][C:5]2=[CH:7][N:8]=[CH:9][N:4]2[CH:3]=1

Participants

5

Reactant 2

HCID 243Benzoic AcidHCID 591684042-Bromoimidazo(4,3-b)(1,3)thiazole-7-carboxylic acid

Product 1

HCID 104654682-Bromoimidazo[5,1-b]thiazoleYield 49.2%

Reagents, catalysts & solvents 2

HCID 131,2,4-TrichlorobenzeneSolventHCID 8058HexaneSolvent

Conditions

Temperature
180 °C

Procedure

A solution of 2-bromoimidazo[5,1-b]thiazole-7-carboxylic acid (32 mg, 0.13 mmol) and benzoic acid (16 mg, 0.13 mmol) dissolved in 1,2,4-trichlorobenzene (1 ml) was stirred at 180° C. for 24 hr. The reaction solution was allowed to cool to room temperature, was diluted with hexane, and was extracted with 2 M hydrochloric acid (3 ml×3). The aqueous layer was neutralized with a 2 M aqueous solution of sodium hydroxide and was extracted with ethyl acetate (5 ml×3). The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under the reduced pressure, and the residue was thoroughly dried to give 2-bromoimidazo[5,1-b]thiazole (13 mg, 49%) as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionwas extracted with 2 M hydrochloric acid (3 ml×3)
  3. extractionwas extracted with ethyl acetate (5 ml×3)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was then removed by distillation under the reduced pressure
  7. customthe residue was thoroughly dried

Sources & evidence

ORD record
ord-3bd36ce111ca4cee80cc8b9652fb51b8
Source dataset
uspto-grants-2010_02
Patent number
US07662841B2

Reaction notes

Loading…