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

HRID 1916733Notes

Reaction equation

HRID 1916733 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-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.O>[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

8

Reactant 4

HCID 807IodineHCID 10906Tert-Butyl nitriteHCID 24477Sodium ThiosulfateHCID 205670295-(4-Chlorophenyl)pyrazin-2-amine

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

With the exclusion of light, 4.9 mL (40.0 mmol) tert-butylnitrite and 7.6 g (30 mmol) iodine are added to a solution of 4.8 g (23.3 mmol) 5-(4-chloro-phenyl)-pyrazin-2-ylamine in 100 mL CCl4 and 50 mL DCM and the reaction mixture is stirred overnight at RT. It is combined with 100 mL water and 50 mL 10% Na2S2O3 solution, the organic phase is separated off, washed again with 50 mL 10% Na2S2O3 solution and twice with 50 mL water and dried over MgSO4. It is filtered through activated charcoal, evaporated down i.vac. and the residue is purified by chromatography (silica gel, gradient: PE to PE/EtOAc 8:2).

Workup

  1. customthe organic phase is separated off
  2. washwashed again with 50 mL 10% Na2S2O3 solution and twice with 50 mL water
  3. dry with materialdried over MgSO4
  4. filtrationIt is filtered through activated charcoal
  5. customevaporated down i.vac
  6. customand the residue is purified by chromatography (silica gel, gradient: PE to PE/EtOAc 8:2)

Sources & evidence

ORD record
ord-b737f8bc55244498810f760a7d37b76a
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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