Iodine → HCID 68417258, compound

HRID 1617121Notes

Reaction equation

HRID 1617121 reaction equation
[I:1]I.[CH3:3][C:4]1[N:9]=[C:8]([NH2:10])[N:7]=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]=1.[OH-].[Na+]>C(Cl)Cl.O>[I:1][C:5]1[C:6]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:7][C:8]([NH2:10])=[N:9][C:4]=1[CH3:3]

Participants

6

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 68415787HCID 68415787, compound

Product 1

HCID 68417258HCID 68417258, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of iodine (11.92 g) in DCM (300 mL) was added to a stirred mixture of the product from step (i) (8.3 g) and sodium hydroxide (3.42 g) in water (200 mL). The reaction mixture was stirred at rt overnight. The organic layer was separated and washed with sodium metabisulfate solution, then brine. The combined organic layers were dried, and the solvent evaporated under reduced pressure. The product was purified by chromatography eluting with DCM:MeOH; 95:5 to give the subtitle compound 11 g. LC-MS m/z 321 ESI

Workup

  1. customThe organic layer was separated
  2. washwashed with sodium metabisulfate solution
  3. customThe combined organic layers were dried
  4. customthe solvent evaporated under reduced pressure
  5. customThe product was purified by chromatography
  6. washeluting with DCM

Sources & evidence

ORD record
ord-ba0e2f293f584fac927e47f18a84b967
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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