Methyl iodide → HCID 23372637, compound

HRID 1862969Notes

Reaction equation

HRID 1862969 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[C:14]([CH3:18])[C:15]([CH3:17])=[CH:16][C:8]=3[NH:7][C:6]=2[N:19]=1.[H-].[Na+].[CH3:22]I>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[N:10]([CH3:22])[C:9]3[CH:13]=[C:14]([CH3:18])[C:15]([CH3:17])=[CH:16][C:8]=3[NH:7][C:6]=2[N:19]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20393048HCID 20393048, compound

Product 1

HCID 23372637HCID 23372637, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture consisting of 38 gm (0.15 mol) of 6,11-dihydro-2,8,9-trimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, 300 ml of dimethyl formamide and 8.4 gm (0.18 mol) of 50% sodium hydride in mineral oil was stirred at room temperature in a nitrogen atmosphere for 30 minutes. Then, a solution of 31.4 gm (0.22 mol) of methyl iodide in 50 ml of dimethyl formamide was added dropwise, and the mixture was heated on an oil bath at 100° C. for 2 hours while stirring. The mixture was then evaporated in vacuo, ice was added to the oily residue, and the mixture was stirred until the residue crystallized. The crystals were collected by suction filtration and recrystallized from n-propanol, yielding 65% of theory of the compound named in the heading, which had a melting point of 217°-219° C.

Workup

  1. temperaturethe mixture was heated on an oil bath at 100° C. for 2 hours
  2. stirringwhile stirring
  3. customThe mixture was then evaporated in vacuo, ice
  4. additionwas added to the oily residue
  5. stirringthe mixture was stirred until the residue
  6. customcrystallized
  7. filtrationThe crystals were collected by suction filtration
  8. customrecrystallized from n-propanol
  9. customyielding 65% of theory of the compound

Sources & evidence

ORD record
ord-00735f7eb9db4d38ac27265968889c81
Source dataset
uspto-grants-1979_09
Patent number
US04167570

Reaction notes

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