Iodine chloride → 1-(4-Amino-3-iodophenyl)-N-methylmethanesulfonamide

HRID 1647770Notes

Reaction equation

HRID 1647770 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[I:14]Cl>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=1[I:14]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 27781314-Amino-N-methylbenzenemethanesulfonamide

Product 1

HCID 107584621-(4-Amino-3-iodophenyl)-N-methylmethanesulfonamideYield 65.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1.06 g (5.31 mmol, 1.0 equiv.) of 4-amino-N-methylbenzenemethanesulfonamide in 20 mL of acetonitrile was added 0.862 g (5.31 mmol, 1.0 equiv.) of iodine monochloride. The reaction was stirred for 15 minutes at room temperature. The mixture was partitioned between 25 mL of ethyl acetate and 15 mL of 20% aqueous sodium thiosulfate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield an oil. The oil was filtered through a plug of silica gel using 40% ethyl acetate in hexane to yield 1.13 g (65%) of 4-amino-3-iodo-N-methylbenzenemethanesulfonamide.

Workup

  1. customThe mixture was partitioned between 25 mL of ethyl acetate and 15 mL of 20% aqueous sodium thiosulfate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto yield an oil
  6. filtrationThe oil was filtered through a plug of silica gel using 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-40f94f7d2fd243309b96b2bcfc7f32ac
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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