Phosphorus oxychloride → HCID 11324874, compound

HRID 1166177Notes

Reaction equation

HRID 1166177 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[C:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])=[N:9][N:10]([CH3:11])[C:5]2=[C:4](O)[CH:3]=1.P(Cl)(Cl)([Cl:23])=O>>[CH3:1][C:2]1[N:7]=[C:6]2[C:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])=[N:9][N:10]([CH3:11])[C:5]2=[C:4]([Cl:23])[CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178428859HCID 178428859, compound

Product 1

HCID 11324874HCID 11324874, compound

Procedure

Intermediate (10) was refluxed in the presence of phosphorous oxychloride (45 ml) for 4 hours. The reaction mixture was cooled to room temperature, concentrated and partitioned between ethyl acetate and saturated sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried, concentrated, and the residue was purified over silica gel (eluent: 10% diethyl ether/hexanes), yielding 5-methyl-7-chloro-1-methyl-3-(2,4-dichlorophenyl)-pyrazolo[4,3-b]pyridine (intermediate 11).

Workup

  1. concentrationconcentrated
  2. custompartitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customthe residue was purified over silica gel (eluent: 10% diethyl ether/hexanes)

Sources & evidence

ORD record
ord-94b2821e1d6f46f492057bcb9d3f2e42
Source dataset
uspto-grants-2003_09
Patent number
US06613777B1

Reaction notes

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