Triphosgene → 6-bromo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

HRID 1777780Notes

Reaction equation

HRID 1777780 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.Cl[C:11](Cl)([O:13]C(=O)OC(Cl)(Cl)Cl)Cl>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:11](=[O:13])[NH:9][N:8]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 115356995-Bromo-2-hydrazinopyridine

Product 1

HCID 120407986-bromo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-oneYield 89.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-2 (2.0 g, 10.6 mmol) in dichloroethane (106 mL) was added triphosgene (3.16 g, 10.64 mmol). The reaction mixture was stirred at room temperature for 3 days. An off-white precipitate formed, which was washed with dichloroethane (100 mL) and dried in vacuo to give 2.03 g (89%) of 3-3 as a tan solid. LC/MS: m/z (M+H)=213.9.

Workup

  1. customAn off-white precipitate formed
  2. washwhich was washed with dichloroethane (100 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-7ce35eda23e141ecaaff9d5588663a9d
Source dataset
uspto-grants-2016_02
Patent number
US09266881B2

Reaction notes

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