Ethanol → HCID 13672737, compound

HRID 867822Notes

Reaction equation

HRID 867822 reaction equation
[CH2:1]([OH:3])[CH3:2].[Na].Cl[C:6]1[N:11]=[C:10]([CH:12]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][CH:7]=1.[H][H]>CS(C)=O.O>[CH2:1]([O:3][C:6]1[N:11]=[C:10]([CH:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=[CH:8][CH:7]=1)[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 5360545Sodium2×HCID 12833242HCID 12833242, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13672737HCID 13672737, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To 30.0 ml of ethanol was added 1.10 g of sodium pellets. After the sodium had dissolved, 10.14 g of 6-chloro-2-(diphenoxymethyl)pyridine in 50 ml of DMSO was added dropwise. The mixture was heated to 80° C. and held there for 24 hours. The reaction was considered complete as seen by the NMR. The reaction mixture was cooled, diluted with water and extracted with methylchloroform. The organic layer was separated and washed with water, dried over anhydrous magnesium sulfate, filtered and the solvent removed by evaporation under reduced pressure. The crude product was then distilled and the portion which distilled over at 157°-165° C. at 0.05 millimeters of mercury was collected. The above indicated product was obtained in a yield of 8.95 g and was found to have a refractive index of n26/d=1.5768. The NMR and Infrared Spectra (IR) were consistent with the structure for the above compound. Upon analysis, the compound was found to have carbon, hydrogen and nitrogen contents of 74.56, 6.01 and 4.19 percent, respectively, as compared with the theoretical contents of 74.77, 5.92 and 4.36 percent, respectively, as calculated for the above named compound (Compound 2).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with methylchloroform
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed by evaporation under reduced pressure
  8. distillationThe crude product was then distilled
  9. distillationthe portion which distilled over at 157°-165° C. at 0.05 millimeters of mercury
  10. customwas collected
  11. customThe above indicated product was obtained in a yield of 8.95 g

Sources & evidence

ORD record
ord-3ae8fa65e6664433894d8d086bc5ce98
Source dataset
uspto-grants-1988_10
Patent number
US04776880

Reaction notes

Loading…