Iodine chloride → 2-Amino-5-iodobenzenesulfonamide

HRID 494490Notes

Reaction equation

HRID 494490 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>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([I:12])=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 728942-Aminobenzenesulfonamide

Product 1

HCID 223240882-Amino-5-iodobenzenesulfonamideYield 55%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 2-aminobenzenesulfonamide (25.0 g, 145.2 mmol) in chloroform (275 mL) at 0° C. was treated with a solution of iodine monochloride (24.75 g, 152.4 mmol) in chloroform (50 mL) dropwise over 1 h. After addition, the solution was allowed to slowly warm to 25° C. over 18 h. The precipitate was collected by filtration and washed with chloroform (3×), saturated sodium bicarbonate solution (1×), and water (4×). After air drying, these procedures afforded the title compound (23.4 g, 55%) as a red solid. 1H NMR (300 MHz, DMSO-d6): δ 6.65 (d, J=8.46 Hz, 1 H) 7.35 (s, 2 H) 7.48 (dd, J=8.82, 2.21 Hz, 1 H) 7.76 (d, J=2.21 Hz, 1 H).

Workup

  1. additionAfter addition
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with chloroform (3×), saturated sodium bicarbonate solution (1×), and water (4×)
  4. customAfter air drying

Sources & evidence

ORD record
ord-25ae197eccaa43fba2a645ff49257fc1
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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