Benzyl Chloride → HCID 178429177, compound

HRID 1898801Notes

Reaction equation

HRID 1898801 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH2:6](Cl)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[CH:15]1[C:21](=[O:22])O[C:18](=O)[CH:17]=[CH:16]1.[CH2:23](N(CC)CC)C.C[O-].[Na+]>CC(O)C.CO.C(OCC)(=O)C.C(O)(=O)C>[CH2:6]([S:4][C:3]1[N:5]=[C:18]2[CH:17]=[C:16]([CH3:23])[CH:15]=[C:21]([OH:22])[N:1]2[N:2]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

10

Reactant 5

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 2723789ThiosemicarbazideHCID 10942334Sodium MethoxideHCID 220869374-Methylglutaconic anhydride

Product 1

HCID 178429177HCID 178429177, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of thiosemicarbazide (50.0 g, 0.554 mol) and benzyl chloride (67.1 g, 0.53 mol) in 2-propanol (1 L) was heated to reflux with stirring for 2 hours. The reaction mixture was then cooled and 4-methylglutaconic anhydride (60.8 g, 0.482 mol) and triethylamine (75 mL, 53.6 g, 0.53 mol) were added. The reaction mixture was again heated at reflux with stirring for an hour. Sodium methoxide in methanol solution (250 mL of 25 percent, 1.09 mol) was then added and the yellow-brown mixture obtained was heated at reflux with stirring for 2.5 hours. The volatiles were removed by evaporation under reduced pressure and the residue obtained was combined with dilute aqueous acetic acid (150 mL) and ethyl acetate. The organic phase was recovered, washed well with water and concentrated by evaporation under reduced pressure. The residue obtained was heated with a heat gun under reduced pressure for 30 minutes until the bubbling had stopped and the reaction mixture had solidified. The mixture was cooled and diluted with methanol and the resulting solids were recovered by filtration to obtain 54.5 g (41 percent of theory) of the title compound as a yellow-brown powder melting at 214°-216° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was then cooled
  4. temperatureThe reaction mixture was again heated
  5. temperatureat reflux
  6. stirringwith stirring for an hour
  7. customthe yellow-brown mixture obtained
  8. temperaturewas heated
  9. temperatureat reflux
  10. stirringwith stirring for 2.5 hours
  11. customThe volatiles were removed by evaporation under reduced pressure
  12. customthe residue obtained
  13. customThe organic phase was recovered
  14. washwashed well with water
  15. concentrationconcentrated by evaporation under reduced pressure
  16. customThe residue obtained
  17. temperaturewas heated with a heat gun under reduced pressure for 30 minutes until the bubbling
  18. temperatureThe mixture was cooled
  19. filtrationthe resulting solids were recovered by filtration

Sources & evidence

ORD record
ord-71f8151f30e4426987390ad6bb5aac87
Source dataset
uspto-grants-1996_11
Patent number
US05571775

Reaction notes

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