Réaction #2006479

Équation de réaction

compound 9

2-Amino-2-methyl-proprionitrile

triethylamine

isocyanate

4-Isocyanato-2-trifluoromethyl-benzonitrile

→

compound 10a

Rendement 47.3%

4-(4,4-Dimethyl-5-imino-2-oxo-1-imidazolidinyl)-2-trifluoromethyl-benzonitrile

Rendement 47.3%

Solvants

1,2 dichloroethane

1,2 dichloroethane

Conditions de réaction

Traitement

1. 1
   Autrethe ice bath was then removed
2. 2
   workup.STIRRINGstirred at room temperature for an additional 30 min
3. 3
   AutreThe solution was then evaporated to dryness
4. 4
   Autrepurified by flash chromatography

Mode opératoire

To a solution of compound 9 (641 mg, 7.62 mmol) and triethylamine (168 mg, 1.66 mmol) in 1,2 dichloroethane (8.4 mL) at 0° C. under argon was dropwise added a solution of the isocyanate 8a (1.54 g, 7.28 mmol) in 1,2 dichloroethane (3.5 mL). The solution was stirred at 0° C. for 35 min and the ice bath was then removed and stirred at room temperature for an additional 30 min. The solution was then evaporated to dryness and purified by flash chromatography using EtOAc/Hexane (6:4) as an eluant to give pure compound 10a (1.02 g, 47%). 1H NMR (300 MHz, Acetone-d6) δ: 1.54 (m, 6H), 7.45 (broad s, 1H), 8.12 (d, 1H, J=8.46 Hz), 8.29 (dd, 1H, J1=6.90 Hz, J2=1.61 Hz), 8.46 (s, 1H), 8.51 (s, 1H).

Source