Hydrochloric Acid → 4-Methyl-5-iodosaccharin

HRID 861822

Reaktionsgleichung

Reaktionsgleichung von HRID 861822
Cl.[CH3:2][C:3]1[C:13](N)=[CH:12][CH:11]=[C:10]2[C:4]=1[C:5](=[O:15])[NH:6][S:7]2(=[O:9])=[O:8].N([O-])=O.[Na+].[I-:20].[K+]>O.C(O)(=O)C>[CH3:2][C:3]1[C:13]([I:20])=[CH:12][CH:11]=[C:10]2[C:4]=1[C:5](=[O:15])[NH:6][S:7]2(=[O:9])=[O:8]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 701876914-Methyl-5-aminosaccharin

Produkt 1

HCID 153462934-Methyl-5-iodosaccharin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 205 ml of glacial acetic acid, 160 ml of water and 40 ml of conc. HCl is initially taken and 23.4 g (0.11 mol) of 4-methyl-5-aminosaccharin are introduced with stirring at 15°-20° C. 7.9 g (0.115 mol) of sodium nitrite are added dropwise to the resulting suspension at 5°-10° C. and it is stirred at 5° C. for 30 min. The diazonium salt, which is present as a suspension, is then added dropwise in portions to a solution, which is warmed to 50° C., of 19.1 g (0.115 mol) of potassium iodide in 170 ml of water, nitrogen being formed. After cooling to room temperature, the deposited product is isolated by filtering off with suction, washed with water and dried under reduced pressure at 50° C. 32.5 g (0.1 mol=91% of theory) of a solid of m.p.: 257°-258° C. are obtained.

Aufarbeitung

  1. stirringit is stirred at 5° C. for 30 min
  2. additionis then added dropwise in portions to a solution, which
  3. customformed
  4. customthe deposited product is isolated
  5. filtrationby filtering off with suction
  6. washwashed with water
  7. customdried under reduced pressure at 50° C
  8. custom32.5 g (0.1 mol=91% of theory) of a solid of m.p.: 257°-258° C. are obtained

Quellen und Nachweise

ORD-Eintrag
ord-50933999bc3147b5a87b83045d98ad61
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716905

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