Phosphorus oxychloride → HCID 178506240, compound

HRID 413255Notes

Reaction equation

HRID 413255 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]2[NH:11][C:10](=O)[NH:9][C:6]2=[N:7][CH:8]=1.P(Cl)(Cl)([Cl:17])=O>[Cl-].C[N+](C)(C)C>[Cl:17][C:10]1[NH:9][C:6]2=[N:7][CH:8]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=[C:5]2[N:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 117153916-Trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 178506240HCID 178506240, compound

Reagents, catalysts & solvents 1

HCID 6379Tetramethylammonium chlorideCatalyst

Procedure

Heat a solution of 6-trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one. (0.6 g, 2.95 mmol) and tetramethylammonium chloride (0.3 g) to 110° C. in phosphorus oxychloride (10 mL) for 10 hours. After cooling, remove the excess POCl3 in vacuo, and then neutralize with saturated NaHCO3, extract with EtOAc. Dry over Na2SO4, concentrate under vacuum to obtain 2-chloro-6-trifluoromethyl-3-H-imidazo[4,5-b]pyridine.

Workup

  1. temperatureAfter cooling
  2. customremove the excess POCl3 in vacuo
  3. extractionextract with EtOAc
  4. dry with materialDry over Na2SO4
  5. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-6d949a50f480480594ec1e33739a1653
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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