Stannous Chloride → 4-(6-Methoxy-1,3-benzothiazol-2-yl)aniline

HRID 2276905Notes

Reaction equation

HRID 2276905 reaction equation
Cl[Sn]Cl.[N+:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][CH:8]=1)([O-])=O>C(O)C>[NH2:4][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][C:15]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 106608526-Methoxy-2-(4-nitrophenyl) benzothiazole

Product 1

HCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineYield 99.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

SnCl2 (5.798 g, 30.58 mmol) was added to 2-(4-nitrophenyl)-6-methoxybenzothiazole (41, 1.459 g, 5.10 mmol) obtained in step 2 dissolved in ethanol (300 mL). The resulting reaction mixture was refluxed for 4 hours under a nitrogen atmosphere and the solvent was removed under reduced pressure. Then, the remaining mixture was dissolved in ethyl acetate and, after washing with 1N NaOH aqueous solution (50 mL) and water (100 mL), water was removed using sodium sulfate. After removing the solvent by distilling under reduced pressure, 2-(4-aminophenyl)-6-methoxybenzothiazole (43, 1.305 g, 99%) was yielded as a yellow solid without further purification.

Workup

  1. customobtained in step 2
  2. customThe resulting reaction mixture
  3. temperaturewas refluxed for 4 hours under a nitrogen atmosphere
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThen, the remaining mixture was dissolved in ethyl acetate
  6. washafter washing with 1N NaOH aqueous solution (50 mL) and water (100 mL), water
  7. customwas removed
  8. customAfter removing the solvent
  9. distillationby distilling under reduced pressure

Sources & evidence

ORD record
ord-a641fa5f040748288ce6b9fda580470f
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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