Sodium Iodide → HCID 58797771, compound

HRID 446200Notes

Reaction equation

HRID 446200 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]=[C:7]([C:9]#[N:10])[S:8][C:4]=2[CH:3]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][CH2:21]Cl)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[C:9]([C:7]1[S:8][C:4]2[CH:3]=[C:2]([O:1][CH2:21][S:20][C:17]3[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=3)[CH:12]=[CH:11][C:5]=2[N:6]=1)#[N:10]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 23610Benzene, 1-chloro-4-((chloromethyl)thio)-HCID 98819122-Cyano-6-hydroxybenzothiazole

Product 1

HCID 58797771HCID 58797771, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 6-hydroxy-2-cyanobenzothiazole (0.45 g, 2.59 mmol), 1-chloro-4-chloromethylthiobenzene (0.50 g, 2.59 mmol), potassium carbonate (0.36 g, 2.61 mmol) and sodium iodide (0.01 g) in acetone (30 ml) was heated to reflux 30 minutes. Upon cooling to room temperature, the insoluble solid was removed by filtration. The solvent of filtrate was removed under reduced pressure, the residue was dissolved minimum amount of acetone with heating. The solution was cooled at 0° C. and yellow crystals were formed immediately. The solid was collected by filtration to give a yield of 37%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux 30 minutes
  3. customthe insoluble solid was removed by filtration
  4. customThe solvent of filtrate was removed under reduced pressure
  5. dissolutionthe residue was dissolved minimum amount of acetone
  6. temperaturewith heating
  7. temperatureThe solution was cooled at 0° C.
  8. customyellow crystals were formed immediately
  9. filtrationThe solid was collected by filtration
  10. customto give a yield of 37%

Sources & evidence

ORD record
ord-3bb07a949ecb40dd9990c4ec5350c998
Source dataset
uspto-grants-2013_07
Patent number
US08476450B2

Reaction notes

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