Sulfuric Acid → HCID 53415966, compound

HRID 225669Notes

Reaction equation

HRID 225669 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1N.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:20].[K+]>O>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[I:20]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 53417040905275-81-2

Product 1

HCID 53415966HCID 53415966, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Procedure

To a stirred suspension of 50.8 mmol 2-fluoro-4,5-dimethyl-phenylamine-(commercial, CAS: 117832-17-4) in 70 ml water was added dropwise at 0° C. a solution of 5 ml concentrated sulfuric acid in 15 ml water. A solution of 66.0 mmol sodium nitrite in 15 ml water was then added dropwise and stirring continued at 0° C. for 60 min. A solution of 173 mmol potassium iodide in 50 ml water was then added dropwise over 30 min while maintaining the reaction temperature between 0 and 5° C. The reaction mixture was then warmed to room temperature and stirred for 3 h before being quenched with aqueous sodium thiosulphite solution and diluted with ethyl acetate. The phases were separated and the organic phase was washed with water and then dried over sodium sulfate and concentrated in vacuo to yield the title compound as a brown solid (69% yield). MS (m/e): 251 ([M+H]+, 100%).

Workup

  1. temperaturewhile maintaining the reaction temperature between 0 and 5° C
  2. stirringstirred for 3 h
  3. custombefore being quenched with aqueous sodium thiosulphite solution
  4. additiondiluted with ethyl acetate
  5. customThe phases were separated
  6. washthe organic phase was washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3848bccb4675415e97fefa6b7cf83b93
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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