Reaction #985257

Reaction equation

2-(4-nitrophenylethenyl)benthiazole

Trans-2-(4-Nitrophenylethenyl)benzothiazole

tin (II) chloride dihydrate

→

product 12

Yield 9.3%

2-(4-Aminophenylethenyl)benzothiazole

Yield 9.3%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturewas refluxed under N2 for 4 hrs
2. 2
   OtherEthanol was removed by vacuum evaporation
3. 3
   workup.DISSOLUTIONThe residue was dissolved into ethyl acetate (20 ml)
4. 4
   Washwashed with NaOH solution (1 N, 3×20 ml) and water (3×20 ml)
5. 5
   Dryingdried over MgSO4
6. 6
   OtherEvaporation to dryness

Procedure

A mixture of 2-(4-nitrophenylethenyl)benthiazole 11 (500 mg, 1.7 mmol) and tin (II) chloride dihydrate (1.18 g, 5.2 mmol) in anhydrous ethanol (20 ml) was refluxed under N2 for 4 hrs. Ethanol was removed by vacuum evaporation. The residue was dissolved into ethyl acetate (20 ml), washed with NaOH solution (1 N, 3×20 ml) and water (3×20 ml), and dried over MgSO4. Evaporation to dryness gave 40 mg (8.0%) of product 12.

Source