Tofisopam → HCID 15587244, compound

HRID 2059130Notes

Reaction equation

HRID 2059130 reaction equation
[Se](=O)=[O:2].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]2[C:20]3[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:25][CH3:26])=[CH:24][C:19]=3[CH:18]([CH2:29][CH3:30])[C:17]([CH3:31])=[N:16][N:15]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]>O1CCOCC1>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]2[C:20]3[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:25][CH3:26])=[CH:24][C:19]=3[CH:18]([CH2:29][CH3:30])[C:17]([CH:31]=[O:2])=[N:16][N:15]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 5502TofisopamHCID 24007Selenium Dioxide

Product 1

HCID 15587244HCID 15587244, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6.05 g of selenium dioxide are added within 1.5 hours to a stirred suspension of 19.1 g (0.05 mole) of 1-(3,4-dimethoxyphenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodiazepine in 150 ml of 80% aqueous dioxane at an inner temperature of 84° to 87° C. The metallic selenium is removed from the mixture by clarification, and the yellow solution is evaporated in vacuo. The thick, honey-like residue is stirred with 100 ml of water, whereupon the title compound separates as a yellow powder. The product is filtered off, washed five times with 10 ml of water each and dried in vacuo. 19.3 g (96%) of crude 1-(3,4-dimethoxyphenyl)-4-formyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodiazepine are obtained; m.p.: 103°-105° C. When recrystallized from acetone and cyclohexane the product melts at 108°-110° C. C22H24N2O5 =396.45.

Workup

  1. customThe metallic selenium is removed from the mixture by clarification
  2. customthe yellow solution is evaporated in vacuo
  3. filtrationThe product is filtered off
  4. washwashed five times with 10 ml of water each and
  5. customdried in vacuo

Sources & evidence

ORD record
ord-90f46b107917429099736f82e0ab11a8
Source dataset
uspto-grants-1982_03
Patent number
US04322346

Reaction notes

Loading…