2-Bromo-1-indanone → HCID 178419873, compound

HRID 865088Notes

Reaction equation

HRID 865088 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.Cl.[NH:13]1[CH:17]=[C:16]([CH2:18][C:19]([NH2:21])=[S:20])[N:15]=[CH:14]1>CC(O)C>[NH:13]1[CH:17]=[C:16]([CH2:18][C:19]2[S:20][C:2]3[CH2:10][C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[C:3]=3[N:21]=2)[N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 1372032-Bromo-1-indanoneHCID 178479561HCID 178479561, compound

Product 1

HCID 178419873HCID 178419873, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.34 g of 2-bromo-1-indanone and 0.26 g of 4-imidazolyl thioacetamide hydrochloride were dissolved in 7 ml of 2-propanol with heating, and the solution was heated for 30 minutes under reflux. After cooling the reaction solution, the precipitated crystals were collected by filtration and washed with ethyl acetate. The collected crystals were partitioned between chloroform and a saturated aqueous sodium bicarbonate solution, and the aqueous layer was extracted with chloroform several times. The combined chloroform layers were washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. By evaporation of the solvent, 0.12 g (32%) of 2-(4-imidazolylmethyl)-8H-indeno[1,2-d]thiazole was obtained. This free base was dissolved in methanol and mixed with 0.055 g of fumaric acid to effect crystallization. The resulting crude crystals were recrystallized from methanol-diethyl ether to obtain 0.10 g of fumarate.

Workup

  1. temperaturewith heating
  2. temperaturethe solution was heated for 30 minutes
  3. temperatureunder reflux
  4. temperatureAfter cooling the reaction solution
  5. filtrationthe precipitated crystals were collected by filtration
  6. washwashed with ethyl acetate
  7. customThe collected crystals were partitioned between chloroform
  8. extractiona saturated aqueous sodium bicarbonate solution, and the aqueous layer was extracted with chloroform several times
  9. washThe combined chloroform layers were washed with a saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customBy evaporation of the solvent

Sources & evidence

ORD record
ord-ab4ab6f8264749c59102bfb043a19a79
Source dataset
uspto-grants-1996_10
Patent number
US05565479

Reaction notes

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