Ethanol → HCID 20551574, compound

HRID 1447165Notes

Reaction equation

HRID 1447165 reaction equation
Br[C:2]1[N:10]2[C:5]([N:6]=[N:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)=[N:4][N:3]=1.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(O)C>O>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:2]2[N:10]3[C:5]([N:6]=[N:7][C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=43)=[N:4][N:3]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 702EthanolHCID 531671-MethylpiperazineHCID 20551567HCID 20551567, compound

Product 1

HCID 20551574HCID 20551574, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12.0 g (0.048 mole) of 1-bromo-s-triazolo[3,4-c]benzo-as-triazine, 40 ml of N-methyl-piperazine and 80 ml of ethanol is refluxed for 2 hours. The solution is poured into water and the product is extracted mit methylene chloride. The solvent is evaporated from the extract and the residue is recrystallized from benzene. 9.7 g (70%) of 1-(N-methyl-piperazino)-s-triazolo[3,4-c]benzo-as-triazine are obtained; m.p.: 162°-163° C. This product is added to a suspension of 12 g (0.068 moles) of sodium dithionite in 100 ml of water, and reduced into the respective dihydro compound under argon atmosphere. The separated precipitate is filtered off, dried, admixed with 50 ml of propionic anhydride, and the mixture is heated at 120° to 125° C. for 2 hours. The reaction mixture is cooled and the separated product is filtered off. 12.3 g (67.0%) of the title compound are obtained; m.p.: 173°-175° C.

Workup

  1. temperatureis refluxed for 2 hours
  2. extractionthe product is extracted
  3. customThe solvent is evaporated from the
  4. extractionextract
  5. customthe residue is recrystallized from benzene

Sources & evidence

ORD record
ord-20c875a2d3de4bb4978a9acb41cbbf73
Source dataset
uspto-grants-1982_02
Patent number
US04316022

Reaction notes

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