Dimethylformamide → 4-Chloro-5-iodopyridin-2-amine

HRID 2215593Notes

Reaction equation

HRID 2215593 reaction equation
CN(C)C=O.[I:6]N1C(=O)CCC1=O.[NH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][N:16]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C>[NH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([I:6])=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 219491214-Chloro-5-iodopyridin-2-amineYield 74.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N,N-Dimethylformamide (47 ml) and N-iodosuccinimide (10.7 g, 47.6 mmol) were added to 2-amino-4-chloropyridine (4.72 g, 36.7 mmol); and the reaction mixture was stirred overnight. An aqueous solution of sodium thiosulfate and ethyl acetate were added thereto; the organic layer was separated, concentrated, and dried over anhydrous sodium sulfate. This was concentrated under reduced pressure; a solvent mixture (ether: hexane=1:1) was added to the residue; and the solid was filtered off to yield the title compound (7.0 g, 27.5 mmol).

Workup

  1. customthe organic layer was separated
  2. concentrationconcentrated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThis was concentrated under reduced pressure
  5. additiona solvent mixture (ether: hexane=1:1) was added to the residue
  6. filtrationand the solid was filtered off

Sources & evidence

ORD record
ord-721250301df54e18991e81272ea3cd96
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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