Benzoyl chloride → 7-Bromo-2-phenyl-[1,2,4]triazolo[1,5-A]pyridine

HRID 1802137Notes

Reaction equation

HRID 1802137 reaction equation
C[C:2]1[CH:7]=[C:6](C)[CH:5]=[C:4]([CH3:9])[C:3]=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[NH2:22].C(Cl)(=O)C1C=CC=CC=1>N1C=CC=CC=1>[Br:21][C:18]1[CH:19]=[CH:20][N:15]2[N:14]=[C:9]([C:4]3[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=3)[N:22]=[C:16]2[CH:17]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 866660161,2-Diamino-4-bromo-pyridinium 2,4,6-trimethyl-benzenesulfonate

Product 1

HCID 677755007-Bromo-2-phenyl-[1,2,4]triazolo[1,5-A]pyridineYield 61.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1,2-Diamino-4-bromopyridinium 2,4,6-trimethylbenzenesulfonate (15.6 g, 40.2 mmole) in pyridine (106 ml) is heated overnight at 100° C. with benzoyl chloride (9.4 ml, 80 mmole) giving a redbrown solution and after 2 hrs a brown suspension. The reaction mixture is concentrated in vacuo and the residue is triturated for 2.5 hr in sat. aqueous ammonium chloride solution (300 ml), while neutralizing to pH 6-7 with sat. aqueous sodium bicarbonate solution. The solid is collected by filtration, washed with water (40 ml) and dried affording 7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (6.78 g, 61.6%) as an off-white solid. mp.: 189-191° C. MS: m/z=276.1, 274.2 (M+H+).

Workup

  1. customgiving a redbrown solution
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customthe residue is triturated for 2.5 hr in sat. aqueous ammonium chloride solution (300 ml)
  4. filtrationThe solid is collected by filtration
  5. washwashed with water (40 ml)
  6. customdried

Sources & evidence

ORD record
ord-e460e77290b8486993baab1c4b133493
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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