2-Bromo-1-indanone → 2-phthalimidomethyl-8H-indeno[1,2-d]thiazole

HRID 356109

Reaction equation

HRID 356109 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.[C:12]1(=[O:26])[N:16]([CH2:17][C:18]([NH2:20])=[S:19])[C:15](=[O:21])[C:14]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:13]12>C(O)(C)C>[C:15]1(=[O:21])[N:16]([CH2:17][C:18]2[S:19][C:2]3[CH2:10][C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[C:3]=3[N:20]=2)[C:12](=[O:26])[C:13]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:14]12

Participants

4

Reactant 2

HCID 1372032-Bromo-1-indanoneHCID 246961282-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanethioamide

Product 1

HCID 189409622-phthalimidomethyl-8H-indeno[1,2-d]thiazoleYield 50.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In 100 ml of isopropanol, 1.64 g of 2-bromo-1-indanone was dissolved. Then, 2.0 g of phthalimidothioacetamide was added, followed by heating under reflux for 6 hours. The precipitate thus formed was collected by filtration and then distributed between chloroform and a saturated aqueous solution of sodium bicarbonate. The organic layer was separated, washed successively with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The solvent was then evaporated, whereby 1.3 g of 2-phthalimidomethyl-8H-indeno[1,2-d]thiazole was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. customThe precipitate thus formed
  4. filtrationwas collected by filtration
  5. customThe organic layer was separated
  6. washwashed successively with water
  7. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  8. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-579db616259141bf9d77890262f0c176
Source dataset
uspto-grants-1998_11
Patent number
US05834499

Linked notes

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