Sodium Hydroxide → 2-(4-Chlorophenyl)-6-(methylthio)benzo[d]thiazole

HRID 1896780Notes

Reaction equation

HRID 1896780 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6](=[S:16])[NH:7][C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>O.C(O)C.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[K+].[K+].[K+].[Fe+3]>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[S:16][C:13]3[CH:12]=[C:11]([S:14][CH3:15])[CH:10]=[CH:9][C:8]=3[N:7]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 576174804-Chloro-N-(4-(methylthio)phenyl)benzothioamide

Product 1

HCID 576174822-(4-Chlorophenyl)-6-(methylthio)benzo[d]thiazoleYield 67.2%

Reagents, catalysts & solvents 3

HCID 26250Potassium ferricyanideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of potassium hexacyanoferrate(III) (670 mg, 2.04 mmol) in water (5 mL) at 90° C. was added dropwise over 5 minutes a solution of 4-chloro-N-(4-(methylthio)phenyl)benzothioamide (150 mg, 0.51 mmol) in ethanol (2 mL) and 3M aqueous sodium hydroxide solution (1.4 mL, 4.08 mmol). The resulting mixture was heated at 90° C. for 30 minutes. After cooling, the precipitate formed was filtered off and washed with water to give a yellow solid. The yellow solid was purified by column chromatography eluting using a gradient (hexanes to ethyl acetate/hexanes 5:95 v/v) to afford 100 mg (67%) of the title compound (LCMS RT=9.37 min, MH+ 292.2)

Workup

  1. temperatureAfter cooling
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customto give a yellow solid
  6. customThe yellow solid was purified by column chromatography
  7. washeluting

Sources & evidence

ORD record
ord-7c90c261aa124935b19fa2f6e63667d7
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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