Ammonium Chloride → HCID 178497694, compound

Participants

Reaction Conditions

Reaction Steps

1.00 g (6.21 mmol) of the compound from Example 47A are initially charged in 18 ml of dry DMF. 2.42 g (37.23 mmol) of sodium azide and 1.99 g (37.23 mmol) of ammonium chloride are then added. The reaction mixture is stirred at 120° C. for 2.5 h. After cooling to RT the mixture is poured into a mixture of 30 ml of ice-water and 10 ml of ethyl acetate. 2.57 g (37.23 mmol) of sodium nitrite are added to this mixture to destroy excess azide. By addition of 6 N hydrochloric acid, the pH is then adjusted to 1-2 and the mixture is stirred at RT for 30 min. The mixture is extracted three times with in each case 20 ml of a 1:1 mixture of ethyl acetate and THF. The precipitate formed is filtered off with suction and dried under reduced pressure. In order to isolate more product, the separated organic phase is washed in each case once with in each case 10 ml of water and saturated aqueous sodium chloride solution. After drying over magnesium sulfate the solvent is removed on a rotary evaporator. Both solids are combined and used for the next step.

Provenance & Evidence