Benzothiazole → HCID 178511489, compound

HRID 339490Notes

Reaction equation

HRID 339490 reaction equation
C(N)(=S)C1C=CC=CC=1.[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[CH:11]1.[Fe-3:19]([C:30]#[N:31])([C:28]#[N:29])([C:26]#[N:27])([C:24]#[N:25])([C:22]#[N:23])[C:20]#[N:21].[K+:32].[K+].[K+].[OH-].[Na+]>O>[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[CH:11]1.[Fe-3:19]([C:28]#[N:29])([C:24]#[N:25])([C:20]#[N:21])([C:22]#[N:23])([C:26]#[N:27])[C:30]#[N:31].[K+:32].[K+:32].[K+:32]

Participants

6

Reactant 4

HCID 7222BenzothiazoleHCID 14798Sodium HydroxideHCID 683563Thiobenzamide2×HCID 178511488HCID 178511488, compound2×

Product 1

HCID 178511489HCID 178511489, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

In this reaction, a thiobenzamide is converted to a benzothiazole in the presence of potassium ferricyanide. In a typical reaction, a thiobenzamide (1 equiv) is dissolved in NaOH (1.5 M, 39 equiv.) and the solution cooled to 5° C. with ice. Potassium ferricyanide in water (20%, 15 vol) is added and the reaction stirred at it for 18 h. The mixture is filtered and the solid washed with H2O. The solid is dissolved in DCM (20 vol), dried (Na2SO4) and the solvent removed under reduced pressure to give the crude benzothiazole product. Column chromatography may be carried out in order to obtain the pure target material.

Workup

  1. customIn this reaction
  2. customIn a typical reaction
  3. filtrationThe mixture is filtered
  4. washthe solid washed with H2O
  5. dissolutionThe solid is dissolved in DCM (20 vol)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-020593f2c3df42c3995f170760703ab1
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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