Iodine → HCID 66753013, compound

HRID 1896342Notes

Reaction equation

HRID 1896342 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[N:8]([C:9](=[O:11])[CH:10]=1)[C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[N:5]2[CH3:16].[I:17]I>C(#N)C>[I:17][C:10]1[C:9](=[O:11])[N:8]2[C:4]([N:5]([CH3:16])[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=32)=[N:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 807IodineHCID 3161846HCID 3161846, compound

Product 1

HCID 66753013HCID 66753013, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Step 2 intermediate (1.2 g, 5.620 mmol) in acetonitrile (15 ml) was added ceric ammonium nitrate (1.53 g, 2.812 mmol) followed by iodine (0.857 g, 3.325 mmol) and refluxed for 2.0 h. After completion of the reaction, the solvent was evaporated and the residue dissolved in ethyl acetate. Combined organic layer was washed with water, saturated NaHSO3 solution, brine and dried and purified to afford the desired compound: 1H NMR (300 MHz, DMSO-d6) δ 2.61 (s, 3H), 3.75 (s, 3H), 7.39-7.42 (s, 1H), 7.52-7.58 (m, 1H), 7.68-7.70 (m, 1H), 8.38-8.41 (s, 1H); ESI-MS (m/z) 340.48 (M+H)+.

Workup

  1. temperaturerefluxed for 2.0 h
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washCombined organic layer was washed with water, saturated NaHSO3 solution, brine
  6. customdried
  7. custompurified

Sources & evidence

ORD record
ord-9928f251b97647958d675e606035f73f
Source dataset
uspto-grants-2013_08
Patent number
US08518955B2

Reaction notes

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