Phosphorus oxychloride → HCID 58216599, compound

HRID 42375Notes

Reaction equation

HRID 42375 reaction equation
[CH2:1]([C:3]1[N:7]2[C:8]3[CH:9]=[C:10]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:11](=O)[NH:12][C:13]=3[CH:14]=[CH:15][C:6]2=[N:5][N:4]=1)[CH3:2].O=P(Cl)(Cl)[Cl:25]>C(#N)C>[Cl:25][C:11]1[N:12]=[C:13]2[C:8](=[CH:9][C:10]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:7]1[C:3]([CH2:1][CH3:2])=[N:4][N:5]=[C:6]1[CH:15]=[CH:14]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67093792HCID 67093792, compound

Product 1

HCID 58216599HCID 58216599, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-ethyl-8-phenyl[1,2,4]triazolo[4,3-a]-1,5-naphthyridin-7(6H)-one (7-4) (70 mg, 0.241 mmol) and POCl3 (3.0 mL, 32.2 mmol) in acetonitrile (2 mL) was heated under microwave irradiation at 150° C. for 1.5 hours. The solvent was removed under reduced pressure, and the residue was diluted with CHCl3, washed with sat. NaHCO3 solution, dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 7-chloro-1-ethyl-8-phenyl[1,2,4]triazolo[4,3-a]-1,5-naphthyridine (7-5) as pale yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with CHCl3
  3. washwashed with sat. NaHCO3 solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ff5c6d426c9b493c99abd161ebcde52c
Source dataset
uspto-grants-2013_09
Patent number
US08536193B2

Reaction notes

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