Reaction #985261

Reaction equation

4-nitrobenzoyl chloride

2-aminothiophenol

→

product

Yield 73.2%

2-(4-Nitrophenyl)benzothiazole

Yield 73.2%

Solvents

benzene

Conditions

Workup

1. 1
   OtherThe reaction was quenched with water (20 mL)
2. 2
   OtherThe aqueous layer was separated
3. 3
   Extractionextracted with ethyl acetate (3×10 ml)
4. 4
   OtherThe combined organic layers were dried
5. 5
   Otherevaporated
6. 6
   OtherThe crude product was purified
7. 7
   Otherwith flush column, (hexane:ethyl acetate=85:15)

Procedure

A solution of 4-nitrobenzoyl chloride (1.49 g, 8.0 mmol) in benzene anhydrous, 10 mL) was added dropwise to 2-aminothiophenol (1.0 g, 8.0 mmol in 10 ml of benzene) at room temperature. The reaction mixture was allowed to stir for 16 hr. The reaction was quenched with water (20 mL). The aqueous layer was separated and extracted with ethyl acetate (3×10 ml). The combined organic layers were dried and evaporated. The crude product was purified with flush column, (hexane:ethyl acetate=85:15) to give 1.5 g (73.2%) of product as light yellow solid.

Source