Nitric Acid → Quintozene

반응식

[Cl:1][C:2]1[C:7](S)=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]([Cl:11])[C:3]=1[Cl:12].[N+:13]([O-])([OH:15])=[O:14].OS(O)(=O)=O.O=S(=O)=O.ClC1C(Cl)=C(Cl)C(Cl)=C(Cl)C=1Cl>>[C:7]1([N+:13]([O-:15])=[O:14])[C:2]([Cl:1])=[C:3]([Cl:12])[C:4]([Cl:11])=[C:5]([Cl:10])[C:6]=1[Cl:9]

참가 물질

반응물 4

HCID 944Nitric Acid

HCID 8370Hexachlorobenzene

HCID 8620Pentachlorothiophenol

HCID 24681Fuming sulfuric acid

생성물 1

HCID 6720Quintozene수율 85%

반응 조건

온도: 55 °C

실험 절차

Pentachlorothiophenol (10.0 g, 0.035 mol) was added to 60.0 g of 99% nitric acid over 20 min at 45°-50° C. followed by heating at reflux (55° C.) for 1.5 hr. At this point 20 mL of 30% by weight oleum was added at such a rate that the temperature was kept at 75° to 80° C. After the addition was complete (approximately 30 min.), the reaction mixture was cooled to room temperature. The product was collected by filtration, and thoroughly washed with water to give after drying in vacuo, 8.6 g (85% yield) of 99.7% PCNB with 0.17% hexachlorobenzene (GC assay). Variations on this one-pot, two-step process were examined and are summarized in TABLE I.