Triethylamine → N-(2-iodo-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide

HRID 541070

Reaction equation

HRID 541070 reaction equation
[I:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].[NH4+].[Cl-]>C(Cl)Cl>[I:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[N:4]([S:20]([CH3:19])(=[O:22])=[O:21])[S:20]([CH3:19])(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 2226292-Iodo-4-nitroaniline

Product 1

HCID 67284344N-(2-iodo-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 2-iodo-4-nitroaniline (25 g; 95 mmol) and triethylamine (43 ml; 312 mmol) in CH2Cl2 (250 ml), a solution containing methanesulphonyl chloride (36 g; 312 mmol) was added dropwise. The reaction mixture was left under stirring at room temperature for 18 hours, then NH4Cl (saturated solution) was added (250 ml). The biphasic solution was transferred into a separating funnel, the organic phase was separated, dried over Na2SO4 and the solvent was removed by evaporation under reduced pressure. The residue was suspended in EtOH (200 ml) and heated under stirring until a yellow solid precipitated. The crude product was filtered, washed with EtOH (750 ml), and dried under vacuum to give N-(2-iodo-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide (32 g) which was used in the following reaction without any further purification.

Workup

  1. additionwas added dropwise
  2. waitThe reaction mixture was left
  3. customThe biphasic solution was transferred into a separating funnel
  4. customthe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed by evaporation under reduced pressure
  7. temperatureheated
  8. stirringunder stirring until a yellow solid
  9. customprecipitated
  10. filtrationThe crude product was filtered
  11. washwashed with EtOH (750 ml)
  12. customdried under vacuum

Sources & evidence

ORD record
ord-6a22ef69760549eb857c99282f72fc4f
Source dataset
uspto-grants-2014_10
Patent number
US08871948B2

Linked notes

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