Triethylamine → 2,2-Dioxo-6-(1,1-dimethylethyl)-8-iodo-1,2,3-benzoxathiazine

HRID 27399

Reaktionsgleichung

Reaktionsgleichung von HRID 27399
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].[I:6][C:7]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[C:9]([CH:10]=O)[C:8]=1[OH:19].C(N(CC)CC)C>C(Cl)Cl>[O:3]=[S:1]1(=[O:4])[N:2]=[CH:10][C:9]2[CH:12]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:14]=[C:7]([I:6])[C:8]=2[O:19]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 127618365-tert-Butyl-2-hydroxy-3-iodobenzaldehyde

Produkt 1

HCID 127618412,2-Dioxo-6-(1,1-dimethylethyl)-8-iodo-1,2,3-benzoxathiazineAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of sulfamoyl chloride (13.8 g, 0.12 mole) in anhydrous methylene chloride (75 ml) is added a solution of 3-iodo-5-(1,1-dimethylethyl)salicylaldehyde (6 g., 0.02 mole) and triethylamine (12.1 g, 0.12 mole) in anhydrous methylene chloride (100 ml.) dropwise with stirring at 20° C. Upon completing the addition, the resulting reaction mixture is stirred at 20° C. for 3 days. Removal of the solvent in vacuo leaves a tacky residue which is partitioned between ether and 2 N hydrochloric acid. After separating the phases, the organic phase is washed with water and saturated brime, dried over sodium sulfate and filtered. Evaporation of the filtrate leaves an oily residue (6 g.) which is chromatographed on silica gel (300 g.) with benzene. Elution with benzene (840 ml.) gives recovered 3-iodo-5-(1,1-dimethylethyl)salicylaldehyde (2.2 g., 37% recovery), m.p. 76°-78° C. Continued elution with benzene (500 ml.) provides an impure solid (2.4 g.) which is triturated with hexane (20 ml.) and filtered to afford the title compound as a pale yellow solid (1.0 g, 14%), m.p. 130°-134° C. Crystallization from hexane benzene (9.1; viv) gives an analytical sample of 2,2-dioxo-6-(1,1-dimethylethyl)-8-iodo-1,2,3-benzoxathiazine, m.p. 135°-136° C.

Aufarbeitung

  1. additionthe addition
  2. customthe resulting reaction mixture
  3. stirringis stirred at 20° C. for 3 days
  4. customRemoval of the solvent in vacuo
  5. customleaves a tacky residue which
  6. customis partitioned between ether and 2 N hydrochloric acid
  7. customAfter separating the phases
  8. washthe organic phase is washed with water and saturated brime
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customEvaporation of the filtrate
  12. customleaves an oily residue (6 g.) which
  13. customis chromatographed on silica gel (300 g.) with benzene
  14. washElution with benzene (840 ml.)
  15. customgives
  16. customrecovered 3-iodo-5-(1,1-dimethylethyl)salicylaldehyde (2.2 g., 37% recovery), m.p. 76°-78° C
  17. washContinued elution with benzene (500 ml.)
  18. customprovides an impure solid (2.4 g.) which
  19. customis triturated with hexane (20 ml.)
  20. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-3e122ab37820459284b931e57f9565ff
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04221790

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