1,3-Dichloro-5,5-dimethylhydantoin → 8-Amino-2-benzylthio-5-chloro[1,2,4]triazolo[1,5-a]pyridine

HRID 963158Notes

Reaction equation

HRID 963158 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([N:8]=[C:9]([S:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:19]N1C(C)(C)C(=O)N(Cl)C1=O.S(=O)(O)[O-].[Na+]>ClCCl>[NH2:1][C:2]1[C:3]2[N:4]([N:8]=[C:9]([S:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:10]=2)[C:5]([Cl:19])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 83601,3-Dichloro-5,5-dimethylhydantoin2×HCID 190807538-Amino-2-benzylthio[1,2,4]triazolo[1,5-a]pyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 190807288-Amino-2-benzylthio-5-chloro[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8-amino-2-benzylthio[1,2,4]triazolo[1,5-a]pyridine (14.0 g, 0.0546 mol) and 1,3-dichloro-5,5-dimethylhydantoin (5.4 g, 0.0273 mol) were combined in 500 mL of dichloromethane and the mixture was heated at reflux with stirring for two hours. Additional 1,3-dichloro-5,5-dimethylhydantoin (5.0 g, 0.025 mol) was added and the reaction was heated with stirring for an additional hour. The reaction mixture was cooled and dilute aqueous sodium bisulfite was added with stirring and allowed to react for an hour. The mixture was then washed with water and the volatiles were removed by evaporation under reduced pressure. The residue obtained was chromatographed on silica gel eluting with dichloromethane to obtain 6.0 g (38 percent of theory) of the title compound as a light tan powder melting at 113°-114° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. temperaturethe reaction was heated
  4. stirringwith stirring for an additional hour
  5. temperatureThe reaction mixture was cooled
  6. stirringwith stirring
  7. customto react for an hour
  8. washThe mixture was then washed with water
  9. customthe volatiles were removed by evaporation under reduced pressure
  10. customThe residue obtained
  11. customwas chromatographed on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-fabb56535f8141c49473a540e72eff0b
Source dataset
uspto-grants-1998_06
Patent number
US05763359

Reaction notes

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