Urea → HCID 22708675, compound

Participants

Reaction Conditions

Reaction Steps

1.66 g (10 mmol) of 5-amino-1-ethyl-2-nitrobenzene (2) are dissolved in a mixture of 3 ml of conc. sulfuric acid and 20 ml of H2O heated to 50° C. and cooled rapidly in an ice bath. At a temperature below 5° C., the mixture is subjected to diazotisation with 760 mg (11 mmol) of sodium nitrite. After 10 minutes, a pinch of urea from a spatula is added and the mixture stirred for another 5 minutes in the ice bath. This reaction mixture is added to a solution of 2.5 g of potassium iodide (15 mmol) in 10 ml of H2O and stirred at room temperature for one hour. The reaction mixture is extracted three times with 50 ml of EE each and the combined organic phases washed once with 50 ml each of In NaOH arid H2O. After drying over Na2SO4, concentration by means of a rotary evaporator is carried out. The crude product is placed on silica gel and purified by flash chromatography (40 g of silica gel, 3.5×13 cm, LM: PE). 1.57 g (5.7 mmol, 57%) of (8) are obtained as a red oil.

Provenance & Evidence