Iodine chloride → 2-Amino-5-iodobenzenesulfonamide

HRID 1767633Notes

Reaction equation

HRID 1767633 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[I:12]Cl>C(Cl)(Cl)Cl>[I:12][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([S:8]([NH2:11])(=[O:9])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 728942-Aminobenzenesulfonamide

Product 1

HCID 223240882-Amino-5-iodobenzenesulfonamideYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a cold (0° C.) stirred solution of 2-aminobenzenesulfonamide (17.2 g; 100 mmol) in CHCl3 (200 ml) was added a solution of iodine monochloride (17.1 g; 105 mmol) in CHCl3 (50 ml) over 1 h. The reaction mixture was slowly warmed up to rt. and left with stirring over night. The reaction mixture was filtered and the isolated solid was washed on the filter with CHCl3 (3×20 ml), NaHCO3 (sat. aq., 1×20 ml), H2O (4×50 ml). The isolated solid was air dried to give 27.3 g (92%) of product.

Workup

  1. waitand left
  2. filtrationThe reaction mixture was filtered
  3. washthe isolated solid was washed on the
  4. filtrationfilter with CHCl3 (3×20 ml), NaHCO3 (sat. aq., 1×20 ml), H2O (4×50 ml)
  5. customdried

Sources & evidence

ORD record
ord-0e4029436c194178a8a4336767761e10
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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