Ethanol → HCID 13672737, compound

HRID 569002Notes

Reaction equation

HRID 569002 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 methyl chloroform. 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 n(26/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 methyl chloroform
  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-e8450e4d43784995b49a7f3bfe65411b
Source dataset
uspto-grants-1988_03
Patent number
US04731107

Reaction notes

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