Iodine → HCID 59485705, compound

HRID 1972190Notes

Reaction equation

HRID 1972190 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[CH2:7].II.[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:25]Cl)(=[O:24])=[O:23])=[CH:20][CH:21]=1>C(#N)C.O>[S:22]([N:25]1[CH2:7][CH:6]1[C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=1)([C:19]1[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 807IodineHCID 31388TosylchloramideHCID 5209863-(Trifluoromethyl)styrene

Product 1

HCID 59485705HCID 59485705, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

3-(Trifluoromethyl)styrene (1.70 mL, 11.5 mmol) is added to a mixture of iodine (0.29 g, 1.15 mmol) and Chloramine-T (3.12 g, 11.5 mmol) in acetonitrile (35 mL). The reaction mixture is stirred at room temperature under a nitrogen atmosphere overnight, then taken in H2O (200 mL) and extracted with CH2Cl2 (3×100 mL). The combined organic layer is washed with brine, dried over MgSO4, concentrated and purified by silica gel chromatography (0˜20% EtOAc/Hexanes) to provide 1-tosyl-2-(3-(trifluoromethyl)phenyl)aziridine (3.44 g, 88% yield) as a colorless oil product.

Workup

  1. extractionextracted with CH2Cl2 (3×100 mL)
  2. washThe combined organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0˜20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-5858fab76eb34f888f3e69f427338262
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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