Iodine → 2-(4-Chlorophenyl)-5-iodopyrazine

HRID 734880Notes

Reaction equation

HRID 734880 reaction equation
C(ON=O)(C)(C)C.[I:8]I.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[CH:19][C:20](N)=[N:21][CH:22]=2)=[CH:13][CH:12]=1.O>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[N:21][C:20]([I:8])=[CH:19][N:18]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 807IodineHCID 962WaterHCID 10906Tert-Butyl nitriteHCID 205670295-(4-Chlorophenyl)pyrazin-2-amine

Product 1

HCID 859696362-(4-Chlorophenyl)-5-iodopyrazine

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

In a flask protected from light, 4.90 mL (40.0 mmol) of tert-butylnitrite and 7.61 g (30.0 mmol) of iodine were added to a solution of 4.80 g (23.5 mmol) of 5-(4-chlorophenyl)pyrazin-2-ylamine in 100 mL of carbon tetrachloride and 50 mL of DCM. The mixture was stirred overnight at RT and then combined with 100 mL of water. The organic phase was washed twice with 50 mL of 10% aqueous sodium thiosulfate solution and 50 mL of water, dried over magnesium sulfate, filtered through activated charcoal, and evaporated down in vacuo. The residue was purified by column chromatography (silica gel, PE→PE/EtOAc 8:2). Yield: 3.40 g (46% of theoretical); C10H6ClIN2 (M=316.525); calc.: molpeak (M+H)+:317/319 (Cl); found: molpeak (M+H)+:317/319 (Cl); Rf value: 0.55 (silica gel, PE/EtOAc 9:1).

Workup

  1. washThe organic phase was washed twice with 50 mL of 10% aqueous sodium thiosulfate solution and 50 mL of water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered through activated charcoal
  4. customevaporated down in vacuo
  5. customThe residue was purified by column chromatography (silica gel, PE→PE/EtOAc 8:2)

Sources & evidence

ORD record
ord-a5fcf8228b004ee08e51b2a61654e541
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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