Hydrochloric Acid → 3-Chloro-1,2-benzisothiazole

HRID 280530

Reaktionsgleichung

Reaktionsgleichung von HRID 280530
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=O)[NH:2]1.O=P(Cl)(Cl)[Cl:13].Cl>O>[Cl:13][C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][N:2]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 175201,2-Benzisothiazol-3(2H)-oneHCID 24813Phosphorus oxychloride

Produkt 1

HCID 5981903-Chloro-1,2-benzisothiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1,2-benzisothiazole-3(2H)-one (Example 1, 818 g, 5.414 moles) and POCl3 (1114 g, 7.26 moles) was heated to 120° over about two hours. HCl evolution began at about 70°. Heat was continued at 120° for another 1.5 hours. The hot solution was poured into 8 liter of H2O at 25°. The temperature was not allowed to exceed 50°. After 30 minutes, the mixture was cooled to 25° (ice addition) and extracted with methylene chloride (4 liter). A dark oil was obtained by evaporation of the methylene chloride in vacuo. This oil was extracted with Skelly B (3×1 liter and 2×500 mL). The turbid extract was treated with Darco G-60 (30 g) and Celite A-545 (20 g) before filtering. The filtrate was evaporated in vacuo to give 743.9 g, 81%, of a yellow oil which readily crystallized. Distillation of the oil at reduced pressure gave 707 g, 77%, b.p. 80°-85° at 0.75 Torr., of colorless distillate which readily crystallized, m.p. 39°-41°.

Aufarbeitung

  1. temperaturewas heated to 120° over about two hours
  2. custombegan at about 70°
  3. temperatureHeat
  4. customto exceed 50°
  5. waitAfter 30 minutes
  6. temperaturethe mixture was cooled to 25°
  7. addition(ice addition)
  8. extractionextracted with methylene chloride (4 liter)
  9. customA dark oil was obtained by evaporation of the methylene chloride in vacuo
  10. extractionThis oil was extracted with Skelly B (3×1 liter and 2×500 mL)
  11. extractionThe turbid extract
  12. additionwas treated with Darco
  13. filtration(30 g) and Celite A-545 (20 g) before filtering
  14. customThe filtrate was evaporated in vacuo
  15. customto give 743.9 g, 81%
  16. customof a yellow oil which readily crystallized
  17. distillationDistillation of the oil at reduced pressure
  18. customgave 707 g, 77%, b.p. 80°-85° at 0.75 Torr
  19. custom, of colorless distillate which readily crystallized

Quellen und Nachweise

ORD-Eintrag
ord-1094e549b40b4755a1b17f76ca1e377f
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04590196

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