Methyl iodide → HCID 20367963, compound

HRID 1834378Notes

Reaction equation

HRID 1834378 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12](=[O:15])[N:13]=[N:14][C:10]3=[CH:9][C:8](=[O:16])[N:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1.[CH3:24]I>>[CH3:24][N:13]1[C:12](=[O:15])[N:11]2[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:23][C:6]=3[N:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:8](=[O:16])[CH:9]=[C:10]2[NH:14]1

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 20373035HCID 20373035, compound

Product 1

HCID 20367963HCID 20367963, compound

Procedure

To an ice-cooled, stirred solution of 3.7 g of 8-chloro-6-phenyl-1H-s-triazolo[4,3-a][1,5]benzodiazepine-1,5-dione in 100 ml of dried and distilled 1,2-dimethoxyethane is added, in a portionwise manner, 0.57 g of a 57% dispersion of sodium hydride in mineral oil. After the evolution of hydrogen has ceased (15 min), a solution of 1.79 g (0.014 mole) of methyl iodide is added, the ice bath removed and stirring continued at room temperature for 2 hours, followed by heating under reflux for 1 hour. The solvent is then removed by distillation. The residue is dissolved in 100 ml of chloroform, washed twice with 100 ml portions of water, dried and concentrated. Treatment of the residue with a small amount of ether precipitates the title compound which is filtered off, dried and recrystallized from ethyl acetate.

Workup

  1. customof dried
  2. distillationdistilled 1,2-dimethoxyethane
  3. additionis added, in a portionwise manner, 0.57 g of a 57% dispersion of sodium hydride in mineral oil
  4. custom(15 min)
  5. customthe ice bath removed
  6. temperatureby heating
  7. temperatureunder reflux for 1 hour
  8. customThe solvent is then removed by distillation
  9. dissolutionThe residue is dissolved in 100 ml of chloroform
  10. washwashed twice with 100 ml portions of water
  11. customdried
  12. concentrationconcentrated
  13. customTreatment of the residue with a small amount of ether precipitates the title compound which
  14. filtrationis filtered off
  15. customdried
  16. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a2a334f9d48b4512a0d65cc78f5af6bd
Source dataset
uspto-grants-1978_01
Patent number
US04070355

Reaction notes

Loading…