Perchloric Acid → 3-Methylthio-11-phenyl-11H-s-triazolo[3,4-b][3]benzazepine

HRID 26507Notes

Reaction equation

HRID 26507 reaction equation
C(O[CH:4](OCC)[CH2:5][N:6]1[C:10]([S:11][CH3:12])=[N:9][N:8]=[C:7]1[CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C.Cl(O)(=O)(=O)=O>>[CH3:12][S:11][C:10]1[N:6]2[C:7]([CH:13]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[CH:4]=[CH:5]2)=[N:8][N:9]=1

Participants

3

Reactant 2

HCID 24247Perchloric AcidHCID 213235154-(2,2-diethoxyethyl)-3-diphenylmethyl-5-methylthio-4H-1,2,4-triazole

Product 1

HCID 213234263-Methylthio-11-phenyl-11H-s-triazolo[3,4-b][3]benzazepine

Procedure

By a procedure similar to that described in Example 1, 20.0 g of the 4-(2,2-diethoxyethyl)-3-diphenylmethyl-5-methylthio-4H-1,2,4-triazole prepared in Reference Example 16 was added to 50 ml of a 70% aqueous solution of perchloric acid under ice-cooling and the mixture was heated at 60°-65° C. for 20 minutes. The cyclization reaction mixture was further treated as described to obtain 3-methylthio-11-phenyl-11H-s-triazolo[3,4-b][3]benzazepine as crystals. Recrystallization from ethanol yielded colorless platelets melting at 169°-170° C.

Workup

  1. customprepared in Reference Example 16
  2. temperaturecooling
  3. temperaturethe mixture was heated at 60°-65° C. for 20 minutes
  4. customThe cyclization reaction mixture
  5. additionwas further treated

Sources & evidence

ORD record
ord-746c85d83ef74cd5b673c12c693ab14f
Source dataset
uspto-grants-1979_04
Patent number
US04150139

Reaction notes

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