Phosgene → 2-Chloro-6-iodo-3-propyl-quinazolin-4-one
Reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=S)[N:6]([CH2:13][CH2:14][CH3:15])[C:5]2=[O:16].C(Cl)([Cl:19])=O>C1(C)C(C)=CC=CC=1>[Cl:19][C:7]1[N:6]([CH2:13][CH2:14][CH3:15])[C:5](=[O:16])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 87.5 °C
Procedure
2,3-Dihydro-6-iodo-3-propyl-2-thioxo4(1H)-quinazolinone (50 g, 0.144 mol) was slurried in xylene (283 g) and heated to 85-90° C. Phosgene (12.0 mL, 0.159 mol) was added. Heating was continued until the thioquinazolinedione was consumed by thin layer chromatography analysis (340 minutes). The excess phosgene was removed by codistillation with xylene at atmospheric pressure. The distillation was ceased when the distillate weight reached 37.9 g. The solution was cooled to room temperature and used directly in Step 3.