N-bromobutanimide → 8-Amino-2-benzylthio-5-bromo[1,2,4]triazolo[1,5-a]pyridine

HRID 1940907Notes

Reaction equation

HRID 1940907 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.[Br:19]N1C(=O)CCC1=O>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]([Br:19])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 190807538-Amino-2-benzylthio[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 214643918-Amino-2-benzylthio-5-bromo[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Amino-2-benzylthio[1,2,4]triazolo[1,5-a]pyridine (25.6 g, 0.1 mol), N-bromosuccinimide (17.8 g, 0.1 mol) and 2 L of dichloromethane were combined with stirring for an hour. The solution was washed with dilute aqueous sodium bisulfite and then with water and the volatiles were removed by evaporation under reduced pressure. The residue obtained was chromatographed on silica gel eluting with 25 percent ethyl acetate in hexane. The product fractions were concentrated by evaporation under reduced pressure and the solid residue obtained was extracted with ether and dried to obtain 17.5 g (52 percent of theory) of the title compound as a light tan powder melting at 125°-126° C.

Workup

  1. washThe solution was washed with dilute aqueous sodium bisulfite
  2. customwith water and the volatiles were removed by evaporation under reduced pressure
  3. customThe residue obtained
  4. customwas chromatographed on silica gel eluting with 25 percent ethyl acetate in hexane
  5. concentrationThe product fractions were concentrated by evaporation under reduced pressure
  6. customthe solid residue obtained
  7. extractionwas extracted with ether
  8. customdried

Sources & evidence

ORD record
ord-1fd487a40ce54d91a6e6baa9f9a23207
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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