Iodine → N-[2-(4-Iodophenyl)ethyl]methanesulfonamide

HRID 2184395Notes

Reaction equation

HRID 2184395 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:4])=[O:3].S(=O)(=O)(O)O.II.[I:21](O)(=O)(=O)=O>C(O)(=O)C.O>[I:21][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 65185Metaperiodic acidHCID 118569Methanesulfonamide, N-(2-phenylethyl)-

Product 1

HCID 22259907N-[2-(4-Iodophenyl)ethyl]methanesulfonamideYield 300.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
72.5 °C

Procedure

To a stirring room temperature solution of (methylsulfonyl)(2-phenylethyl)amine (205 g, 1.03 moles), water (200 mL), 95% sulfuric acid (111 g, 1.08 moles) in acetic acid (1 L), was added iodine (111 g, 0.438 mol) and periodic acid (H5IO6, 45.6 g, 0.206 mol). The reaction mixture was warmed to 70-75° C. for 3 h. The heat was removed and the dark violet reaction mixture was allowed to proceed overnight at room temperature. Potassium hydroxide pellets (85%, 143 g, 2.16 moles) were added to neutralized the sulfuric acid and then enough saturated aqueous sodium sulfite was added to decolorize the mixture to afford a white suspension. The suspension was cooled to 15° C. and filtered. The filter cake was triturated thoroughly with water and was then dissolved in CH2Cl2 (1 L) and extracted with additional water (2×200 mL). The organic phase was concentrated under reduced pressure to provide the intermediate title compound, [2-(4-iodophenyl)ethyl](methylsulfonyl)amine, (201 g, 60.2%) as a white powder. 1H NMR (CDCl3, 300 MHz) δ 7.64 (d, 2H, J=4.8), 6.97 (d, 2H, J=5.1), 4.37 (br t, 1H, J=4), 3.36 (app. q, 2H, J=3.9), 2.85 (s, 3H), 2.82 (t, 2H, J=3.9).

Workup

  1. customThe heat was removed
  2. additionwere added
  3. additionenough saturated aqueous sodium sulfite was added
  4. customto afford a white suspension
  5. temperatureThe suspension was cooled to 15° C.
  6. filtrationfiltered
  7. customThe filter cake was triturated thoroughly with water
  8. dissolutionwas then dissolved in CH2Cl2 (1 L)
  9. extractionextracted with additional water (2×200 mL)
  10. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-484618be100045618a47e1edd5d7d15b
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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