Phosphorus oxychloride → HCID 58577766, compound

HRID 587594Notes

Reaction equation

HRID 587594 reaction equation
O=[C:2]1[N:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[NH:3]1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:2]1[N:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 67335103ethyl 2-(2-oxo-1H-imidazo[4,5-b]pyridin-3(2H)-yl)acetate

Product 1

HCID 58577766HCID 58577766, compound

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl (2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)acetate (14.5 g) and phosphoryl chloride (100 mL) was stirred at 100° C. overnight. The mixture was poured into ice, neutralized with saturated sodium bicarbonate solution and extracted with AcOEt. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was diluted with AcOEt and insoluble crystals were removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluted with 10%-40% AcOEt in hexane) to give the title compound (5.46 g).

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was diluted with AcOEt and insoluble crystals
  7. customwere removed by filtration
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by column chromatography (silica gel, eluted with 10%-40% AcOEt in hexane)

Sources & evidence

ORD record
ord-1bc8701400874ac3abc497590f276edb
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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