Phosphorus oxychloride → HCID 58149900, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N+:21]([O-])=[CH:22]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].P(Cl)(Cl)([Cl:30])=O>>[Cl:30][C:22]1[C:23]2[C:18](=[C:17]([C:14]3[N:13]=[C:12]([C:4]4[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[C:2]([Cl:1])[CH:3]=4)[O:16][N:15]=3)[CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:20][N:21]=1Participants
3
Conditions
- Temperature
- 65 °C
Procedure
5-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)isoquinoline 2-oxide (D6; 1.18 g, 3.09 mmol) and phosphorus oxychloride (5.76 ml, 61.8 mmol) was stirred under an atmosphere of argon at room temperature for 4 hours. The mixture was then heated to 65° C. for 15 minutes, the phosphorus oxychloride evaporated under reduced pressure, and the residue, azeotroped with toluene and dried under vacuum overnight. The pale yellow solid residue was dissolved in dichloromethane (50 ml) and stirred with 2M NaOH (10 ml). The organic layer was separated, dried with MgSO4 and evaporated to dryness under reduced pressure to give a pale yellow solid (1.14 g) which was chromatographed over silica eluting with dichloromethane to give the title compound as a white solid (0.85 g).