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

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

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

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

Sources & evidence

ORD record: ord-521c5174335347a4bae92bc57db22b50
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06943159B1

Reaction notes

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Participants

Reactant 2

HCID 24640Iodine chloride

HCID 114365382-Amino-4-methylbenzenesulfonamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×