Reaction #163826

Reaction equation

1,4-diaminobenzene

ethyl isocyanate

potassium carbonate

→

4-(ethylaminocarbonylamino)aniline

Yield 62.0%

Solvents

THF

Conditions

Workup

1. 1
   OtherThe reaction mixture was partitioned in 1N HCl solution (80 mL)
2. 2
   ExtractionThe aqueous layer was extracted with ethyl acetate (4×80 mL)
3. 3
   OtherThe combined organic layers was dried
4. 4
   Otherevaporated
5. 5
   Otherrecrystallized from MeOH/CH2Cl2/hexanes

Procedure

A mixture of 1,4-diaminobenzene (4 g, 37 mmol), ethyl isocyanate (1 mL, 12.6 mmol) and potassium carbonate (8.72 g, 63 mmol) in THF (20 mL) was stirred at room temperature overnight. The reaction mixture was partitioned in 1N HCl solution (80 mL) and ethyl acetate (80 mL). The aqueous layer was extracted with ethyl acetate (4×80 mL). The combined organic layers was dried, evaporated, recrystallized from MeOH/CH2Cl2/hexanes to give 4-(ethylaminocarbonylamino)aniline (1.4 g, 62%) as a beige solid.

Source