Potassium Iodide → 2-Iodobenzene-1-sulfonamide

HRID 1781783Notes

Reaction equation

HRID 1781783 reaction equation
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]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 728942-AminobenzenesulfonamideHCID 23668193Sodium Nitrite

Product 1

HCID 28248922-Iodobenzene-1-sulfonamideYield 69.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

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 0.2 N sodiumthiosulfate solution and twice with water, evaporated to dryness to give 4 g of a light yellow compound (62% yield). m.p.=197°-198° C., IR (nujol): 3360, 3255, 1562 cm-1, MS (M+): 283

Workup

  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 0.2 N sodiumthiosulfate solution and twice with water
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-b8d9322228f549dd86a0241ae2cb5e96
Source dataset
uspto-grants-1997_05
Patent number
US05633400

Reaction notes

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