Phosphorus oxychloride → HCID 18446571, compound
Reaction equation
[C:1]([C:3]1[C:4]2[S:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)=[CH:10][C:5]=2[C:6](=O)[NH:7][CH:8]=1)#[N:2].P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:6]1[C:5]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[S:12][C:4]=2[C:3]([C:1]#[N:2])=[CH:8][N:7]=1Participants
3
Procedure
7-Cyano-2-(4′-t-butylphenyl)-4-oxo-4,5-dihydrothieno[3,2-c]-pyridine was dissolved in phosphorus oxychloride (25 mL) and the resulting solution heated at reflux for 2 h. After this time the mixture was poured into ice and stirred for 1 h. The precipitated solid was filtered and washed with water, drying by suction in air at room temperature affording 1.05 g of 101. 1H NMR (300 MHz, d6-DMSO) δ 8.83 (s, 1H), 8.11 (s, 1H), 7.92 (d, 2H), 7.56 (d, 2H), 1.34 (s, 9H).
Workup
- temperaturethe resulting solution heated
- temperatureat reflux for 2 h
- additionAfter this time the mixture was poured into ice
- filtrationThe precipitated solid was filtered