Phosphorus oxychloride → HCID 117974229, compound

HRID 2272923Notes

Reaction equation

HRID 2272923 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:5]2[NH:4][C:3]1=O.P(Cl)(Cl)([Cl:18])=O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:18][C:3]1[N:2]([CH3:1])[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:5]2[N:4]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 117974232HCID 117974232, compound

Product 1

HCID 117974229HCID 117974229, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 1.09 g of 3-methyl-6-trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one, one drop of dimethylformamide and 10 g of phosphorus oxychloride was stirred at 100° C. for 3 hours. The cooled reaction mixture was poured to a saturated aqueous sodium bicarbonate solution, and the mixture was extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.61 g of 2-chloro-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

Workup

  1. customThe cooled reaction mixture
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3aff0ac0f0ba45ef8d77e4f556130336
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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