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

HRID 26496Notes

Reaction equation

HRID 26496 reaction equation
[CH2:1]([OH:4])CO.[OH-].[K+].CSC1[N:18]2[C:12]([CH2:13][C:14]3[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=3[CH:16]=[CH:17]2)=[N:11][N:10]=1.Cl>O>[N:11]1[NH:10][C:1](=[O:4])[N:18]2[CH:17]=[CH:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[CH2:13][C:12]=12

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 213234063-methylthio-11H-s-triazolo[3,4-b][3]benzazepine

Product 1

HCID 130667602,11-dihydro-3H-s-triazolo[3,4-b][3]benzazepin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2 ml of ethylene glycol was added 0.2 g of potassium hydroxide, followed by addition of 0.23 g of 3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine. The mixture was stirred at 150°-160° C. for 2 hours, after which water was added. The mixture was made acidic with 4N-hydrochloric acid and extracted with chloroform. The chloroform layer was washed with water and dried over Na2SO4. The solvent was evaporated off and the residue was treated with ethyl acetate. By the above procedure was obtained 2,11-dihydro-3H-s-triazolo[3,4-b][3]benzazepin-3-one as crystals. Recrystallization from methanol yielded light-brown needles melting at 207°-208° C. The following compounds were produced by procedures similar to that of the above Reference Example.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with water
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated off
  5. additionthe residue was treated with ethyl acetate

Sources & evidence

ORD record
ord-b2a796f2b1ed403fa68ebf793d57b8b8
Source dataset
uspto-grants-1979_04
Patent number
US04150139

Reaction notes

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