Dimethylformamide → 2,11-dihydro-2-methyl-3H-s-triazolo[3,4-b][3]benzazepin-3-one

HRID 1414722Notes

Reaction equation

HRID 1414722 reaction equation
[N:1]1[NH:2][C:3](=[O:15])[N:4]2[CH:10]=[CH:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[CH2:6][C:5]=12.[CH3:16]N(C)C=O.[OH-].[Na+].CI>O>[CH3:16][N:2]1[C:3](=[O:15])[N:4]2[C:5]([CH2:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=[CH:10]2)=[N:1]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 130667602,11-dihydro-3H-s-triazolo[3,4-b][3]benzazepin-3-one

Product 1

HCID 130667612,11-dihydro-2-methyl-3H-s-triazolo[3,4-b][3]benzazepin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8 parts of 2,11-dihydro-3H-s-triazolo-[3,4-b][3]benzazepin-3-one in 80 volume parts of dimethylformamide is added 9 volume parts of 5N aqueous sodium hydroxide solution and then 3 volume parts of methyl iodide is added dropwise under stirring. After stirring for 1 hour, the reaction mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate layer is washed with water and the solvent is distilled off. The precipitate is collected by filtration to give 2,11-dihydro-2-methyl-3H-s-triazolo[3,4-b][3]benzazepin-3-one as crystals. Recrystallization from isopropyl ether gives light-brown needles melting at 123° -124° C.

Workup

  1. stirringAfter stirring for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer is washed with water
  4. distillationthe solvent is distilled off
  5. filtrationThe precipitate is collected by filtration

Sources & evidence

ORD record
ord-d48b59df7efa49cf8c9a8645b6cea471
Source dataset
uspto-grants-1977_01
Patent number
US04002638

Reaction notes

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