Methyl iodide → HCID 68135917, compound

HRID 1658788Notes

Reaction equation

HRID 1658788 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:6][C:7]([N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]2[C:20](=O)[NH:21][N:22]=[C:12]2[C:11]2[CH:24]=[CH:25][CH:26]=[N:27][C:10]1=2)=[O:8])[CH3:5].[CH3:28]I>CN(C)C=O>[CH3:28][N:21]1[CH2:20][N:13]2[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:9]([C:7](=[O:8])[CH2:6][N:4]([CH3:5])[CH3:3])[C:10]3[N:27]=[CH:26][CH:25]=[CH:24][C:11]=3[C:12]2=[N:22]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21525513HCID 21525513, compound

Product 1

HCID 68135917HCID 68135917, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (0.178 g., 4.21 mmoles of a 57% dispersion in mineral oil) is added to a solution of 2,9-dihydro-9-[(dimethylamino)acetyl]-3H-pyrido[3,2-c]-s-triazolo[4,3-a][1,5]benzodiazepin-3-one (4.21 mmoles) in 50 ml. of dimethylformamide and the mixture is heated at 95° C. for 35 minutes. The mixture is cooled to 50° C., a solution of methyliodide (4.21 mmole) is added and heating is continued at 95° C. for 21 hours. The mixture is evaporated and methylene chloride-water is added to the residue. The organic layer is separated and extracted three times with 10 ml. portions of 10% aqueous hydrochloric acid. The acid extract is cooled, made alkaline with 15% aqueous sodium hydroxide and the basic mixture is extracted with methylene chloride. The extract is washed with saturated salt solution, dried over anhydrous magnesium sulfate and evaporated. Crystallization of the residue from ether gives 2,9-dihydro-2-methyl-9-[(dimethylamino)acetyl]-3 H-pyrido[3,2-c]-s-triazolo[4,3-a]-[1,5]benzodiazepine.

Workup

  1. temperatureheating
  2. customThe mixture is evaporated
  3. additionmethylene chloride-water is added to the residue
  4. customThe organic layer is separated
  5. extractionextracted three times with 10 ml
  6. extractionThe acid extract
  7. temperatureis cooled
  8. extractionthe basic mixture is extracted with methylene chloride
  9. washThe extract is washed with saturated salt solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated
  12. customCrystallization of the residue from ether

Sources & evidence

ORD record
ord-7fcfd7b14dff41d384ae656102bfe661
Source dataset
uspto-grants-1976_06
Patent number
US03966736

Reaction notes

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