Potassium Iodide → 2-Iodobenzene-1-sulfonamide

HRID 53406

Reaktionsgleichung

Reaktionsgleichung von HRID 53406
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].N([O-])=O.[Na+].[I-:16].[K+]>OS(O)(=O)=O.O>[I:16][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9]

Komponenten

6

Edukt 3

HCID 4875Potassium IodideHCID 728942-AminobenzenesulfonamideHCID 23668193Sodium Nitrite

Produkt 1

HCID 28248922-Iodobenzene-1-sulfonamideAusbeute 69,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-aminobenzene sulfonamide (3.5 g) in conc. H2SO4, 98% (25 ml) are heated at 60° to give a clear solution. 20 g of ice is then added and the solution is cooled to 0° C. NaNO2 (1.45 g) in water (4 ml) is added dropwise very carefully without exceeding 5°-6° C. The reaction mixture is stirred at 5°-6° C. for 3 hours. A solution of potassium iodide (3.75 g) in H2O (25 ml) is then introduced dropwise and the obtained red mixture is stirred for 18 hours. H2O (50 ml) is added and the obtained precipitate is filtered, washed several times in water. The obtained solid is dissolved in ethyl acetate, washed once with 0.2N sodiumthiosulfate solution and twice with water, evaporated to dryness to give 4 g of a light yellow compound (62% yield).

Aufarbeitung

  1. customto give a clear solution
  2. customwithout exceeding 5°-6° C
  3. stirringthe obtained red mixture is stirred for 18 hours
  4. filtrationthe obtained precipitate is filtered
  5. washwashed several times in water
  6. dissolutionThe obtained solid is dissolved in ethyl acetate
  7. washwashed once with 0.2N sodiumthiosulfate solution and twice with water
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-13be94cbd57447c6bb28e782fbef3cb4
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618975

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