Iodine chloride → 5-Iodo-4-methyl-2-aminobenzenesulfonamide

HRID 1767665Notes

Reaction equation

HRID 1767665 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:4]([NH2:12])[CH:3]=1.[I:13]Cl>C(Cl)(Cl)Cl>[I:13][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([NH2:12])=[C:5]([S:8]([NH2:11])(=[O:9])=[O:10])[CH:6]=1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 114365382-Amino-4-methylbenzenesulfonamide

Product 1

HCID 223240635-Iodo-4-methyl-2-aminobenzenesulfonamideYield 62.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred suspension of 4-methyl-2-aminobenzenesulfonamide (620 mg; 3.3 mmol) in CHCl3 (7 ml) at 0° C. was added a solution of iodine monochloride (1.6 g; 9.9 mmol) in CHCl3 (7 ml). The reaction mixture was stirred at 0° C. until H-NMR indicated full conversion of starting material. The reaction mixture was filtered and the isolated solid washed with small volumes of CHCl3, NaHCO3 (sat. aq.), H2O and air dried to give 640 mg (62%) of product.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe isolated solid washed with small volumes of CHCl3, NaHCO3 (sat. aq.), H2O and air
  3. customdried

Sources & evidence

ORD record
ord-eaec7a9510814141b8cd7f26a8ff4623
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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