2,5-Dimethylaniline → (4-Iodo-2,5-Dimethylphenyl)Amine

HRID 1017795Notes

Reaction equation

HRID 1017795 reaction equation
I(Cl)(=O)=O.[I:5](Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][C:27]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:28]=1[NH2:29].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CO.ClCCl.O>[CH3:26][C:27]1[CH:33]=[C:32]([I:5])[C:31]([CH3:34])=[CH:30][C:28]=1[NH2:29]

Participants

8

Reactant 4

HCID 72592,5-DimethylanilineHCID 11430Potassium CarbonateHCID 656671Sodium PyrosulfiteHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 4770984(4-Iodo-2,5-Dimethylphenyl)Amine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

25.0 g (71.8 mmol) of benzyltrimethylammonium dichloriodate and 12.8 g (92.5 mmol) of potassium carbonate are added to a solution of 8.8 ml of (70.8 mmol) of 2,5-dimethylaniline in 250 ml of methanol and 600 ml of dichloromethane and stirred for 1 hour at ambient temperature. Then the inorganic salts are suction filtered and the solvent is distilled off. The residue is combined with a solution of 13.5 g (70.8 mmol) of sodium pyrosulphite in 640 ml of water and extracted with ether. The combined organic extracts are dried over sodium sulphate and evaporated down. The crude product is triturated with petroleum ether, suction filtered and dried.

Workup

  1. filtrationfiltered
  2. distillationthe solvent is distilled off
  3. extractionextracted with ether
  4. dry with materialThe combined organic extracts are dried over sodium sulphate
  5. customevaporated down
  6. customThe crude product is triturated with petroleum ether, suction
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-31f9fcdb7d0f4fb996b038725fc7271d
Source dataset
uspto-grants-2002_11
Patent number
US06479524B1

Reaction notes

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