Oxalyl chloride → HCID 19966727, compound

HRID 1451165Notes

Reaction equation

HRID 1451165 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=O)[C:6]([Cl:8])=[O:7].[N:11]1([N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])C=[CH:14][CH:13]=[CH:12]1>ClCCCl>[Cl:8][C:6]([C:5]1[N:11]([N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])[CH:12]=[CH:13][CH:14]=1)=[O:7]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19966727HCID 19966727, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A suspension of anhydrous aluminium chloride (3.1 g; 4.7×5 mM) in 20 ml of 1,2-dichloroethane was cooled with ice to 0°-5° C., and oxalyl chloride (3 g; 4.7×5 mM) was added dropwise to the suspension. After stirred at 0°-5° C. for 20 minutes, a suspension of N-(1H-pyrrol-1-yl)phthalimide (IX-I; 1.0 g; 4.7 mM) in 1,2-dichloroethane was added thereto. Thereafter, the mixture was stirred for 50 minutes with slowly raising the temperature to room temperature. The reaction mixture was poured into ice water and insoluble materials was removed by filteration. To the filtrate was added ethyl acetate with thoroughly stirring to separate an organic phase. The organic phase was dried with sodium sulfate, and the solvent was then removed by distillation to obtain the compound (IX-61)

Workup

  1. temperaturewas cooled with ice to 0°-5° C.
  2. additionwas added
  3. stirringThereafter, the mixture was stirred for 50 minutes
  4. customwas removed by filteration
  5. additionTo the filtrate was added ethyl acetate
  6. stirringwith thoroughly stirring
  7. customto separate an organic phase
  8. dry with materialThe organic phase was dried with sodium sulfate
  9. customthe solvent was then removed by distillation
  10. customto obtain the compound (IX-61)

Sources & evidence

ORD record
ord-a17717f6d2c243d39b3779caf51ce7fc
Source dataset
uspto-grants-1997_02
Patent number
US05604178

Reaction notes

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