Iodine → HCID 86710143, compound

HRID 1051141Notes

Reaction equation

HRID 1051141 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[NH:10][C:9]=1[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[I:17]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[CH2:1]([C:8]1[C:13](=[O:14])[C:12]([I:17])=[C:11]([CH3:15])[NH:10][C:9]=1[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 70819321HCID 70819321, compound

Product 1

HCID 86710143HCID 86710143, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3 (100 mg, 0.45 mmol) in acetonitrile (2.5 mL) was added ceric ammonium nitrate (25 mg, 0.045 mmol) followed by iodine (126 mg, 0.495 mmol). The reaction mixture was stirred at 70° C. under nitrogen for 7 h. After completion of the reaction, the mixture was cooled to room temperature and treated with an ice-cold aqueous solution of sodium thiosulfate with stirring. The mixture was extracted with portions of ethyl ether. The combined organic phase was dried over anhydrous MgSO4 and concentrated under diminished pressure to afford a crude residue. The residue was purified by chromatography on a silica gel column. Elution with hexane/ethyl acetate gave 3-heptyl-5-iodo-2,6-dimethylpyridin-4(1H)-one (5) as a light yellow solid: yield 119 mg (74%); silica gel TLC Rf 0.45 (1:1 hexane/ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 0.88-0.91 (m, 3H), 1.29-1.35 (m, 10H), 2.33 (s, 3H) and 2.54-2.56 (m, 5H).

Workup

  1. customAfter completion of the reaction
  2. temperaturethe mixture was cooled to room temperature
  3. stirringwith stirring
  4. extractionThe mixture was extracted with portions of ethyl ether
  5. dry with materialThe combined organic phase was dried over anhydrous MgSO4
  6. concentrationconcentrated under diminished pressure
  7. customto afford a crude residue
  8. customThe residue was purified by chromatography on a silica gel column
  9. washElution with hexane/ethyl acetate

Sources & evidence

ORD record
ord-3fd29e7940434134b1f61c2a1939a4f6
Source dataset
uspto-grants-2016_07
Patent number
US09388163B2

Reaction notes

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