Ammonia → 6-methyl-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine

HRID 26505Notes

Reaction equation

HRID 26505 reaction equation
[CH2:1]([C:8]1[N:12]([CH2:13][C:14](=O)[CH3:15])[C:11]([S:17][CH3:18])=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N>>[CH3:15][C:14]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH2:1][C:8]2=[N:9][N:10]=[C:11]([S:17][CH3:18])[N:12]2[CH:13]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 213233951-(3-benzyl-5-methylthio-4H-1,2,4-triazol-4-yl)-2-propanone

Product 1

HCID 213233406-methyl-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine

Procedure

To 0.3 g of the 1-(3-benzyl-5-methylthio-4H-1,2,4-triazol-4-yl)-2-propanone obtained in Reference Example 7 was added 15.0 g of polyphosphoric acid and the mixture was heated on an oil bath at 160°-170° C. for 4 hours. The reaction mixture was poured into ice-water, neutralized with concentrated aqueous ammonia 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 isopropyl ether. By the above procedure, 6-methyl-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine was obtained as crystals. Recrystallization from ethyl acetate gave colorless platelets melting at 129°-130° C.

Workup

  1. temperaturethe mixture was heated on an oil bath at 160°-170° C. for 4 hours
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated off
  6. additionthe residue was treated with isopropyl ether

Sources & evidence

ORD record
ord-a3973deac5094e0aa627c18882a384f9
Source dataset
uspto-grants-1979_04
Patent number
US04150139

Reaction notes

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