Succinic anhydride → HCID 68528479, compound

HRID 1932478Notes

Reaction equation

HRID 1932478 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:10]([F:21])[CH:9]=1)=[O:6].[C:26]1(=[O:32])[O:31][C:29](=[O:30])[CH2:28][CH2:27]1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:26](=[O:32])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:17][CH:16]=2)=[C:10]([F:21])[CH:9]=1)=[O:6]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 6451240Aluminum(III) ChlorideHCID 68526847HCID 68526847, compound

Product 1

HCID 68528479HCID 68528479, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension consisting of 3,4-dichloro-3′-fluoro-4′-phenoxybenzanilide (5.05 g, 13.4 mmol) and succinic anhydride (1.48 g, 14.8 mmol) in 1,2-dichloroethane (25 mL) was added aluminum chloride (6.26 g, 47.0 mmol) under ice cooling, and the resulting mixture was stirred at the same temperature for 5 minutes, and then at room temperature for 1.5 hours. The resulting reaction solution was poured into ice water, and the resulting solid was collected by filtration. To the solid was added 50% aqueous acetone (200 mL), and the resulting solution was refluxed for 0.5 hours, then cooled. The obtained solid was collected by filtration, to thereby yield 6.30 g of the title compound.

Workup

  1. waitat room temperature for 1.5 hours
  2. customThe resulting reaction solution
  3. filtrationthe resulting solid was collected by filtration
  4. additionTo the solid was added 50% aqueous acetone (200 mL)
  5. temperaturethe resulting solution was refluxed for 0.5 hours
  6. temperaturecooled
  7. filtrationThe obtained solid was collected by filtration

Sources & evidence

ORD record
ord-0781ede8781a4c4784b418e5aec13c32
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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