Phosphorus oxychloride → HCID 23155135, compound

HRID 1912805Notes

Reaction equation

HRID 1912805 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH:17]=[CH:16][N+:15]([O-])=[CH:14][C:13]=3[N:12]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:14]1[C:13]2[N:12]=[CH:11][N:10]([C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[C:18]=2[CH:17]=[CH:16][N:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 23155151HCID 23155151, compound

Product 1

HCID 23155135HCID 23155135, compound

Conditions

Temperature
80 °C

Procedure

In 5 mL of phosphorus oxychloride, 42 mg (0.164 mmol) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine 5-oxide was dissolved and the solution was stirred at 80° C. for 14 hours. Excess reagent was distilled under reduced pressure, and the residue was partitioned between ethyl acetate (10 mL×2) and a sodium hydrogencarbonate aqueous solution (10 mL). The combined organic layers were washed with a saturated sodium chloride solution, dried on anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was separated by a silica gel column (Si-10, a product of Kusano Co., Ltd., column 30 cm, dichloromethane:methanol=19:1) to obtain 45 mg (quantitative) of 4-chloro-1-(4-nitrophenyl)-1H-imidazo-[4,5-c]pyridine as a pale yellow solid.

Workup

  1. distillationExcess reagent was distilled under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (10 mL×2)
  3. washThe combined organic layers were washed with a saturated sodium chloride solution
  4. dry with materialdried on anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated by a silica gel column (Si-10

Sources & evidence

ORD record
ord-f5087ab5d0e34a8b971e41a77710752f
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

Loading…