Dimethyl Sulfate → HCID 13748840, compound

HRID 986206Notes

Reaction equation

HRID 986206 reaction equation
S(OC)(O[CH3:5])(=O)=O.[O:8]=[C:9]1[NH:16][CH2:15][CH:14]2[CH:10]1[CH2:11][CH2:12][CH2:13]2.[OH-].[Na+]>C1C=CC=CC=1>[CH3:5][O:8][C:9]1[CH:10]2[CH:14]([CH2:15][N:16]=1)[CH2:13][CH2:12][CH2:11]2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 13748839HCID 13748839, compound

Product 1

HCID 13748840HCID 13748840, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Over a period of 1 hour, 94.7 ml of dimethyl sulfate are added dropwise to a solution, maintained at reflux, of 125.2 g of 2-oxo-3-azabicyclo(3,3,0)octane in 350 ml of anhydrous benzene. Reflux is then maintained for 4 hours. After cooling, the reaction mixture is poured onto 100 ml of concentrated sodium hydroxide solution. The organic layer is decanted, and the aqueous layer is extracted twice with 200 ml of benzene each time. The benzene extracts are combined, dried over magnesium sulfate and concentrated in vacuo and the residue is distilled. In this manner 79.5 g of 2-methoxy-3-azabicyclo(3,3,0)oct-2-ene are obtained, b.p.: 64°-68° C., nD23 =1.4718.

Workup

  1. temperaturemaintained
  2. temperatureReflux
  3. temperatureis then maintained for 4 hours
  4. temperatureAfter cooling
  5. customThe organic layer is decanted
  6. extractionthe aqueous layer is extracted twice with 200 ml of benzene each time
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. distillationthe residue is distilled

Sources & evidence

ORD record
ord-e6390873eaf54f4bab162286250901c3
Source dataset
uspto-grants-1987_12
Patent number
US04711885

Reaction notes

Loading…