Tetrahydrofuran → 2-(3-ethyl-2(3H)-benzothiazolylidene)-1,3-dihydro-1-oxo-3-phenyl-2H-indene

HRID 430411

Reaction equation

HRID 430411 reaction equation
[H-].[Na+].C1COCC1.CC1C=CC(S([O-])(=O)=O)=CC=1.[CH2:19]([N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[S:23][CH2+:22]1SCC)[CH3:20].[C:33]1([CH:39]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:41](=[O:48])[CH2:40]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CO.O>[CH2:19]([N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[S:23][C:22]1=[C:40]1[CH:39]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:41]1=[O:48])[CH3:20]

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 981461-Indanone, 3-phenyl-

Product 1

HCID 539763982-(3-ethyl-2(3H)-benzothiazolylidene)-1,3-dihydro-1-oxo-3-phenyl-2H-indeneYield 22.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Procedure

A flask was charged with 1.2 g (30 mmol) of sodium hydride (60 wt %), and 100 ml of THF was added thereto in a stream of nitrogen and stirred to make a suspension. While ice-cooling, to this was added 5.9 g (15 mmol) of 3-ethyl-2-(ethylthio)-2(3H)-benzothiazolium 4-methylbenzenesulfonate powder in small portions. Next, to this was added dropwise 50 ml of THF solution containing 6.24 g (30 mmol) of 3-phenyl-1-indanone. The reaction solution was stirred under ice-cooling for 3 hours and at room temperature for 3 hours and then mixed with 20 ml of methanol. When the reaction solution was poured in small portions into a stirred mixed solution of 100 ml of water and 100 ml of methanol, yellow crude crystals were obtained. The crude crystals were suspended in 100 ml of methanol, refluxed, purified and then collected by filtration, thereby obtaining 1.23 g (3.33 mmol) of yellow crystals of D14. Yield was 22%. Its structure was identified by nuclear magnetic resonance spectrum, infrared absorption spectrum, mass spectrometry spectrum and elemental analysis (found; carbon 78.00%, hydrogen 5.15% calcd.; carbon 78.02%, hydrogen 5.18%).

Workup

  1. additionwas added
  2. temperatureWhile ice-cooling
  3. stirringThe reaction solution was stirred under ice-
  4. additionWhen the reaction solution was poured in small portions into a stirred
  5. customyellow crude crystals were obtained
  6. temperaturerefluxed
  7. custompurified
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4fb51b97eda943aab1c554d8cb9388b5
Source dataset
uspto-grants-2001_11
Patent number
US06322950B1

Linked notes

Loading…