N,N-Dimethylaniline → 2-Benzylthio-5-chloro-7-methyl[1,2,4]triazolo[1,5-a]pyridine

HRID 963151Notes

Reaction equation

HRID 963151 reaction equation
CN(C)C1C=CC=CC=1.[CH2:10]([S:17][C:18]1[N:28]=[C:21]2[CH:22]=[C:23]([CH3:27])[CH:24]=[C:25](O)[N:20]2[N:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCCCCC.P(Cl)(Cl)([Cl:37])=O>C(OCC)(=O)C>[CH2:10]([S:17][C:18]1[N:28]=[C:21]2[CH:22]=[C:23]([CH3:27])[CH:24]=[C:25]([Cl:37])[N:20]2[N:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 178429177HCID 178429177, compound

Product 1

HCID 190807642-Benzylthio-5-chloro-7-methyl[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N,N-Dimethylaniline (21.9 g, 0.18 mol) was added slowly to a mixture of 2-benzylthio-5-hydroxy-7-methyl[1,2,4]triazolo[1,5-a]pyridine (44.5 g, 0.164 mol) in 150 mL of phosphorus oxychloride with stirring. The mixture was heated at reflux with stirring for 20 hours. The excess phosphorus oxychloride was then removed by evaporation under reduced pressure. The residue obtained was dissolved in ethyl acetate, washed well with water and quickly concentrated by evaporation under reduced pressure to drive off the excess water. The residue was again dissolved in ethyl acetate and the resulting mixture was filtered with suction through a bed of silica gel. The filtrate was concentrated by evaporation under reduced pressure and the residue obtained was mixed with hexane. The resulting mixture was filtered to recover the solids and dried to obtain the 37.5 g (79 percent of theory) of the title compound as a tan powder melting at 108°-110° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. stirringwith stirring for 20 hours
  4. customThe excess phosphorus oxychloride was then removed by evaporation under reduced pressure
  5. customThe residue obtained
  6. washwashed well with water
  7. concentrationquickly concentrated by evaporation under reduced pressure
  8. dissolutionThe residue was again dissolved in ethyl acetate
  9. filtrationthe resulting mixture was filtered with suction through a bed of silica gel
  10. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  11. customthe residue obtained
  12. filtrationThe resulting mixture was filtered
  13. customto recover the solids
  14. customdried

Sources & evidence

ORD record
ord-de1aa12c8194405082ff58e61bf4434f
Source dataset
uspto-grants-1998_06
Patent number
US05763359

Reaction notes

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