Sodium Hydroxide → 6-Methoxy-2-(4-nitrophenyl) benzothiazole

HRID 2276904Notes

Reaction equation

HRID 2276904 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[S:20])[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C.O>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([C:10]2[S:20][C:7]3[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[N:9]=2)=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10661000HCID 10661000, compound

Product 1

HCID 106608526-Methoxy-2-(4-nitrophenyl) benzothiazoleYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

N-(4-Methoxyphenyl)-4-nitrobenzothioamide (39, 6.0 g, 20.81 mmol) was drenched in ethanol (1 mL) and 30% NaOH aqueous solution (6.66 g, 166.48 mmol) was added. The resulting reaction mixture was diluted with water (60 mL) and K3Fe(CN)6 (18.0 g, 41.62 mmol) dissolved in water (50 mL) was slowly added at 90° C. After heating the reaction mixture for 1 hour at 90° C. and cooling to room temperature, the produced precipitate was filtered and washed with water. After dissolving the remaining precipitate in ethyl acetate and removing drying over sodium sulfate, column chromatography yielded the target compound 2-(4-nitrophenyl)-6-methoxybenzothiazole (41, 1.718 g, 30%) as a yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. additionwas slowly added at 90° C
  3. temperaturecooling to room temperature
  4. filtrationthe produced precipitate was filtered
  5. washwashed with water
  6. dissolutionAfter dissolving the remaining precipitate in ethyl acetate
  7. customremoving
  8. dry with materialdrying over sodium sulfate, column chromatography

Sources & evidence

ORD record
ord-e16620e159bb487097ae4710ffdb1528
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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