Sodium Iodide → HCID 58510520, compound

HRID 1169530Notes

Reaction equation

HRID 1169530 reaction equation
F[B-](F)(F)F.N#[O+].[CH3:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH3:24])[C:14]=1[C:15]1[C:20]([CH3:21])=[CH:19][C:18](N)=[CH:17][C:16]=1[CH3:23].[Na+].[I-:26].[Al].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C>[I:26][C:18]1[CH:19]=[C:20]([CH3:21])[C:15]([C:14]2[C:9]([CH3:8])=[CH:10][N:11]=[CH:12][C:13]=2[CH3:24])=[C:16]([CH3:23])[CH:17]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 5359268AluminumHCID 11137142Nitrilooxonium tetrafluoroborateHCID 595503394-(3,5-Dimethyl-pyridin-4-yl)-3,5-dimethyl-phenylamine

Product 1

HCID 58510520HCID 58510520, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Conditions

Temperature
-30 °C

Procedure

To a stirring suspension of nitrosonium tetrafluoroborate (0.876 g, 7.50 mmol) in dry acetonitrile (10 mL) was added dropwise via syringe a solution of 10 (0.904 g, 4.00 mmol) in dry acetonitrile (15 mL) under N2 at −30° C. The reaction mixture was next stirred at −30° C. for 1 h. To the resulting yellow solution was then added dropwise in the dark a solution of anhydrous NaI (1.125 g, 7.50 mmol) in dry acetonitrile (10 mL) under N2 at −30° C. The reaction mixture was covered with aluminum foil, allowed to gradually warm to room temperature, and stirred at room temperature overnight. The resulting red solution was next decolorized using an aqueous solution of Na2S2O3 and extracted with chloroform (50 mL×3). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with 8:1 chloroform: ethyl acetate, to give 0.96 g (72%) of the title compound as a yellow solid: mp 242-243° C.; 1H NMR (400 MHz, CDCl3): δ 8.397 (s, 2H), 7.520 (s, 2H), 1.908 (s, 6H), 1.838 (s, 6H); 13C NMR (100 MHz, CDCl3): δ 148.611, 147.520, 136.983, 136.774, 130.841, 93.681, 19.488, 16.758; MS(ESI): m/z 338.2[(M+H)+, 100]; Anal. Calcd. for C15H16IN: C, 53.43; H, 4.78; N, 4.15. Found; C, 52.91; H, 4.72; N, 4.07.

Workup

  1. temperatureto gradually warm to room temperature
  2. stirringstirred at room temperature overnight
  3. extractionextracted with chloroform (50 mL×3)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography on silica gel
  9. washeluting with 8:1 chloroform

Sources & evidence

ORD record
ord-2467e9484284466b8569b1cbf6b9a770
Source dataset
uspto-grants-2010_11
Patent number
US07824582B2

Reaction notes

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