Chloride → HCID 22022460, compound

HRID 1374970Notes

Reaction equation

HRID 1374970 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=[O:22].CC[O:32][CH2:33][CH3:34]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([C:34](=[O:22])[C:33](=[O:32])[N:9]2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 5

HCID 312ChlorideHCID 3283Diethyl EtherHCID 7416NitrobenzeneHCID 7544N-Phenyl-m-anisidineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22022460HCID 22022460, compoundYield 50%

Procedure

A solution of N-(3-methoxyphenyl)-N-phenylamine (1.14 g, 5.72 in ether (3 mL) was added to a solution of oxylyl chloride (728 g, 5.75 mmol)and heated at reflux for 1 hour. The resulting mixture was cooled to room temperature, concentrated to dryness, and redissolved in nitrobenzene (35 mL). The solution was added to a solution of AlCl3 in nitrobenzene (0.762 g, 5.72 mmol), and the resulting mixture was heated at 70° C. for 16 hours. The crude product was concentrated in vacuo and purified by column chromatography [eluent: EtOAc/hexane (1:1)], giving the desired product (60 mg, 50%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. concentrationconcentrated to dryness
  4. dissolutionredissolved in nitrobenzene (35 mL)
  5. temperaturethe resulting mixture was heated at 70° C. for 16 hours
  6. concentrationThe crude product was concentrated in vacuo
  7. custompurified by column chromatography [eluent: EtOAc/hexane (1:1)]

Sources & evidence

ORD record
ord-0713518d58da4a378cffa475a4b1501d
Source dataset
uspto-grants-2007_01
Patent number
US07166635B2

Reaction notes

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