Potassium Carbonate → HCID 15230480, compound

HRID 1464293Notes

Reaction equation

HRID 1464293 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[N:13]([CH2:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[C:12]3=[O:26])=[CH:4][CH:3]=1.I[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>[Cu].ClC1C=CC=CC=1Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[N:13]([CH2:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[C:12]3=[O:26])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 2855718-Crown-6HCID 15230481HCID 15230481, compound

Product 1

HCID 15230480HCID 15230480, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 85 mg of 5-[N-(4-chlorophenyl) amino]-2-(3-pyridylmethyl)-1H-isoindole-1,3 (2H)-dione, 71 mg of iodobenzene, 30 mg of copper dust, 12 mg of 18-crown-6 (1,4,7,10,13,16-hexaoxacyclooctadecane), 128 mg of potassium carbonate and 2 ml of 1,2-dichlorobenzene was refluxed under heating for 7 hours. After finishing the reaction, the insoluble material was filtered off, and the filtrate was concentrated in vacuo. The resultant residue was chromatographed on a column of silica gel, eluting with chloroform and methanol (100:1) to give 96 mg of the titled compound.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 7 hours
  3. customthe reaction
  4. filtrationthe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resultant residue was chromatographed on a column of silica gel
  7. washeluting with chloroform and methanol (100:1)

Sources & evidence

ORD record
ord-de9e5cbbc5414d0b84fff68f16ceea49
Source dataset
uspto-grants-1994_04
Patent number
US05304556

Reaction notes

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