Thioacetamide → HCID 9903258, compound

HRID 2269293Notes

Reaction equation

HRID 2269293 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:11])[CH:8]=2)[C:3]1=O.[C:13]([NH2:16])(=[S:15])[CH3:14]>CC(C)=O>[ClH:11].[Cl:11][C:7]1[CH:6]=[CH:5][C:4]2[C:3]3[N:16]=[C:13]([CH3:14])[S:15][C:2]=3[CH2:10][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 113340692-Bromo-5-chloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 9903258HCID 9903258, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1 g of 2-bromo-5-chloroindan-1-one is stirred with 0.31 g of thioacetamide in 100 ml of acetone at room temperature for 5 h. The precipitate is filtered off with suction, washed with acetone and dried in vacuo. The hydrobromide is suspended in ethyl acetate and neutralized with triethylamine, and the ethyl acetate solution is washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The free base is dissolved in tetrahydrofuran, and an excess of ethereal HCl is added to this solution. The mixture is stirred at room temperature for 2 h and then concentrated in vacuo. The residue (hydrochloride of 6-chloro-2-methyl-8,8a-dihydroindeno [1,2-d]thiazol-3a-ol) is heated under reflux in 30 ml of glacial acetic acid for 4 h. The solvent is removed in vacuo, the residue is stirred with diisopropyl ether and 6-chloro-2-methyl-8H-indeno[1,2-d]thiazole hydrochloride is obtained with a melting point of 135° C.

Workup

  1. filtrationThe precipitate is filtered off with suction
  2. washwashed with acetone
  3. customdried in vacuo
  4. washthe ethyl acetate solution is washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe free base is dissolved in tetrahydrofuran
  9. additionan excess of ethereal HCl is added to this solution
  10. concentrationconcentrated in vacuo
  11. temperatureThe residue (hydrochloride of 6-chloro-2-methyl-8,8a-dihydroindeno [1,2-d]thiazol-3a-ol) is heated
  12. temperatureunder reflux in 30 ml of glacial acetic acid for 4 h
  13. customThe solvent is removed in vacuo
  14. stirringthe residue is stirred with diisopropyl ether

Sources & evidence

ORD record
ord-a5c80171237a41e0a7e814ae2d00ae31
Source dataset
uspto-grants-2001_12
Patent number
US06329407B1

Reaction notes

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