HCID 12877066, compound → 74852-82-7

HRID 1164226Notes

Reaction equation

HRID 1164226 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:5]=[C:4](SC)[N:3]=1>[Ni].CO>[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 12877066HCID 12877066, compound

Product 1

HCID 1287706874852-82-7Yield 47%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 20 parts of 4-[5-methyl-3-(methylthio)-1H-1,2,4-triazol-1-yl]benzenamine, 15 parts of Raney-nickel catalyst and 400 parts of methanol is stirred and refluxed for 2 hours. The Raney-nickel is filtered off and another 15 parts of the catalyst are added. Stirring at reflux is continued for 4 hours. The reaction mixture is filtered, washed on the filter with methanol and the filtrate is evaporated. The residue is crystallized from a mixture of 4-methyl-2-pentanone, 2,2'-oxybispropane and petroleumether. The product is filtered off and dried, yielding 7.6 parts (47%) of 4-(5-methyl-1H-1,2,4-triazol-1-yl)benzenamine; mp. 145° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe Raney-nickel is filtered off
  3. additionanother 15 parts of the catalyst are added
  4. stirringStirring
  5. temperatureat reflux
  6. filtrationThe reaction mixture is filtered
  7. washwashed on the
  8. filtrationfilter with methanol
  9. customthe filtrate is evaporated
  10. customThe residue is crystallized from a mixture of 4-methyl-2-pentanone, 2,2'-oxybispropane and petroleumether
  11. filtrationThe product is filtered off
  12. customdried

Sources & evidence

ORD record
ord-000661adac584a59bc7b6acd19fd325d
Source dataset
uspto-grants-1983_01
Patent number
US04368200

Reaction notes

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