Sodium Acetate → (2E,3E,5Z)-5-(1,1-dioxido-3-oxo-1-benzothien-2(3H)-ylidene)-2-(3-ethyl-1,3-benzothiazol-2(3H)-ylidene)pent-3-enenitrile

HRID 76813Notes

Reaction equation

HRID 76813 reaction equation
[I-].[C:2]([CH2:4][C:5]1[S:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[N+:9]=1[CH2:10][CH3:11])#[N:3].CO/[CH:18]=[CH:19]/[CH:20]=[C:21]1\[S:22](=[O:32])(=[O:31])[C:23]2[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=2[C:25]\1=[O:26].C(Cl)(Cl)Cl.CO.C([O-])(=O)C.[Na+]>CO>[O:31]=[S:22]1(=[O:32])[C:23]2[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=2[C:25](=[O:26])/[C:21]/1=[CH:20]/[CH:19]=[CH:18]/[C:4](=[C:5]1\[S:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[N:9]\1[CH2:10][CH3:11])/[C:2]#[N:3]

Participants

6

Reactant 4

HCID 517045Sodium AcetateHCID 21584188Chloroform methanolHCID 58153059HCID 58153059, compoundHCID 67262733HCID 67262733, compound

Product 1

HCID 25155717(2E,3E,5Z)-5-(1,1-dioxido-3-oxo-1-benzothien-2(3H)-ylidene)-2-(3-ethyl-1,3-benzothiazol-2(3H)-ylidene)pent-3-enenitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a one-necked round bottom 100-mL flask equipped with magnetic stir bar and reflux condenser were added 2-(cyanomethyl)-3-ethyl-1,3-benzothiazol-3-ium iodide (1.00 g, 3.03 mmol), (2Z)-2-[(2E)-3-methoxyprop-2-en-1-ylidene]-1-benzothiophen-3-(2H)-one 1,1-dioxide (1.00 g, 4.00 mmol) and CHCl3-MeOH mixture (1:1, 20 mL). The flask was heated on an oil bath with stirring until boiling began, and a solution of sodium acetate (320 mg, 4.00 mmol) in 10 mL of methanol was added to the flask. The stirring was continued under reflux for an additional 30 min. The flask was cooled to room temperature and the precipitated solid was filtered, washed with methanol and dried. Green crystals. The yield was 730 mg (57% of theory).

Workup

  1. customIn a one-necked round bottom 100-mL flask equipped with magnetic stir bar
  2. temperaturereflux condenser
  3. temperatureThe flask was heated on an oil bath
  4. temperatureunder reflux for an additional 30 min
  5. filtrationthe precipitated solid was filtered
  6. washwashed with methanol
  7. customdried

Sources & evidence

ORD record
ord-d80d9f75d2f64180ae500e87393d67c8
Source dataset
uspto-grants-2014_09
Patent number
US08835632B2

Reaction notes

Loading…