Phosphorus pentachloride → HCID 13770502, compound

HRID 236363Notes

Reaction equation

HRID 236363 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]([OH:22])=O)=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:23])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]3[O:12][CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:20](=[O:22])[C:9]=3[CH:10]=2)[CH2:5][C:4]1=[O:23])[CH3:2]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 6451240Aluminum(III) ChlorideHCID 13934850HCID 13934850, compound

Product 1

HCID 13770502HCID 13770502, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 5.0 g. (16.1 mmoles) of 1-ethyl-5-(2-carboxybenzyloxy)oxindole in 100 ml. of methylene chloride was added 3.34 g. (16.1 mmoles) of phosphorous pentachloride and the reaction mixture allowed to stir 30 minutes at 25° C. The reaction mixture was cooled to --15° C. and 8.56 g. (64.4 mmoles) of aluminum chloride was added. The resulting mixture was allowed to stir at room temperature for 30 minutes and was then added to ice. The organic phase was separated, dried over magnesium sulfate and concentrated to give the desired product which was recrystallized from ethyl acetate-hexane, 2.3 g (69% yield), m.p. 186.5°-188.5° C.

Workup

  1. additionTo a suspension of 5.0 g
  2. temperatureThe reaction mixture was cooled to --15° C. and 8.56 g
  3. stirringto stir at room temperature for 30 minutes
  4. additionwas then added to ice
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-31506542d3e44d998babce761c1fb6c8
Source dataset
uspto-grants-1987_02
Patent number
US04644005

Reaction notes

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