ammonia in 1,2-dichloro-ethane T=-30 - 20°C; Heating / reflux;

ammonium chloride in methanol; thionyl chloride; anhydrous dichloroethane

manganese(IV) oxide; oxygen; urea T=150°C; P=3800.26 Torr; 4 h; Autoclave;

1: Heating 2: 74 percent / saturated aq. NH3 / 24 h / Ambient temperature View Scheme

ammonium hydroxide 24 h; Ambient temperature;

manganese(IV) oxide; oxygen; urea T=150°C; P=3800.26 Torr; 3 h; Autoclave;

1: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 2: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 3: 66 percent / potassium permanganate / H2O / 3 h / Heating 4: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight View Scheme

1: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 2: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min View Scheme

potassium hydroxide; bromine 1.) RT, 1 h, 2.) 70 deg C, 15 min;

triethylamine; trifluoroacetic anhydride in dichloromethane T=0°C; Dehydration;