1,1'-Carbonyldiimidazole → 6-Iodo-[1,2,4]triazolo[4,3-a]pyridin-3(2h)-one

HRID 1372482Notes

Reaction equation

HRID 1372482 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.C1N=CN([C:15](N2C=NC=C2)=[O:16])C=1>ClCCl>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:15](=[O:16])[NH:9][N:8]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 223971882-Hydrazinyl-5-iodopyridine

Product 1

HCID 587793486-Iodo-[1,2,4]triazolo[4,3-a]pyridin-3(2h)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-iodo-2-hydrazinopyridine (470 mg, 2 mmol) in dichloromethane (30 mL) was added a solution of N,N-carbonyldiimidazole (389 mg, 2.4 mmol) in 20 mL of dichloromethane. After stirring at room temperature for 2 h, the mixture was washed sequentially with water, 0.5N aqueous hydrochloric acid and saturated aqueous sodium bicarbonate solution. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure to afford the product. The resultant yellow crystals that precipitated from the aqueous phase upon standing overnight were collected and dried in vacuo to afford additional product. LC/MS 261.8 (M+1).

Workup

  1. washthe mixture was washed sequentially with water, 0.5N aqueous hydrochloric acid and saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customto afford the product
  5. customThe resultant yellow crystals that precipitated from the aqueous phase
  6. waitupon standing overnight
  7. customwere collected
  8. customdried in vacuo
  9. customto afford additional product

Sources & evidence

ORD record
ord-3f3ceabebe694876b3ffc340dd9289b1
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

Loading…