Water → HCID 15230482, compound

HRID 1464294Notes

Reaction equation

HRID 1464294 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[N+]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[N:18]([CH2:24][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)[C:17]2=[O:31])([O-])=O.O>CN(C)C=O.C(OCC)(=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:22]2[CH:21]=[C:20]3[C:16](=[CH:15][CH:14]=2)[C:17](=[O:31])[N:18]([CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[C:19]3=[O:23])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7815p-ChlorothiophenolHCID 24758Sodium hydrideHCID 869878HCID 869878, compound

Product 1

HCID 15230482HCID 15230482, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 42 mg of sodium hydride (about 60%) in 10 ml of dimethylformamide was added 150 mg of 4-chlorothiophenol, and the resultant mixture was stirred at 60° C. for 30 minutes and mixed with 300 mg of 5-nitro-2-(3-pyridylmethyl)-1H-isoindole-1,3 (2H)-dione. The mixture was heated at 120° C. for 8 hours under stirring, mixed with water and shaken with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and the resultant, residue was chromatographed on a column of silica gel, eluting with chloroform to give 201 mg of the titled compound.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated in vacuo
  3. customthe resultant, residue was chromatographed on a column of silica gel
  4. washeluting with chloroform

Sources & evidence

ORD record
ord-5ab88f183228410d8e9d086ae1a6f981
Source dataset
uspto-grants-1994_04
Patent number
US05304556

Reaction notes

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