Sodium Iodide → HCID 19025817, compound

HRID 1033249Notes

Reaction equation

HRID 1033249 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.[C:12]1([C:18]2[N:19]=[C:20]([SH:29])[NH:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CCCCCC.CS(C)=O.C(OCC)(=O)C>[C:12]1([C:18]2[N:19]=[C:20]([S:29][CH2:4][CH2:5][CH2:6][CH2:11][CH2:10][O:3][CH2:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=3)[NH:21][C:22]=2[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 76752-(2-Hydroxyethyl)pyridineHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 178527825HCID 178527825, compound

Product 1

HCID 19025817HCID 19025817, compoundYield 9.5%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (2.24 g of 50% w/w slurry in mineral oil, 46.7 mmol) was washed in hexane and dried under vacuum. Dimethylsulfoxide (30 mL) was added, followed by a solution of 2-(2-hydroxyethyl)pyridine (5.00 mL, 44.4 mmol) in dimethylsulfoxide (20 mL) dropwise. After stirring for 2 hours, the mixture was treated with 1H-bromo-5-chloropentane (6.00 mL, 45.5 mmol), and was heated to 80° C. for 18 hours. The resulting mixture was cooled, treated with 4,5-diphenyl-2-mercapto-1H-imidazole (7.00 g, 27.7 mmol), potassium carbonate (7.00 g, 50.6 mmol) and sodium iodide (1 g), and heated again to 80° C. for an additional 24 hours. The mixture was cooled, poured into 400 mL ethyl acetate, and washed with water (4×400 mL). The ethyl acetate layer was washed with saturated aqueous sodium chloride (200 mL), dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was separated by flash chromatography, and the product was further purified by preparative thin-layer chromatography to afford the title compound as an oil (940 mg, 2.12 mmol, 8%). 1H NMR (CDCl3): 11.53 (1H, br s); 8.48 (1H, dt, J=5.1, 0.9 Hz); 7.61-7.06 (13H, m); 3.70 (2H, t, J=6.6 Hz); 3.37 (2H, t, J=6.0 Hz); 2.97 (2H, t, J=7.3 Hz); 2.94 (2H, t, J=6.6 Hz); 1.68-1.30 (6H, m). High-resolution mass spectrum: calculated for C27H30N3OS 444.2110, observed 444.2101, difference 1.9 ppm.

Workup

  1. customdried under vacuum
  2. additionDimethylsulfoxide (30 mL) was added
  3. temperatureThe resulting mixture was cooled
  4. temperatureheated again to 80° C. for an additional 24 hours
  5. temperatureThe mixture was cooled
  6. washwashed with water (4×400 mL)
  7. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride (200 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was separated by flash chromatography
  12. customthe product was further purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-e343e6780e03431885f9c3b701775879
Source dataset
uspto-grants-1994_05
Patent number
US05310748

Reaction notes

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