Methanesulfonyl chloride → HCID 54281668, compound

HRID 862386Notes

Reaction equation

HRID 862386 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]=[C:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])=[CH:4][CH:3]=1.[S:19](Cl)([CH3:22])(=[O:21])=[O:20]>N1C=CC=CC=1>[S:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[C:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])=[CH:17][CH:18]=1)([CH3:22])(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 53702970HCID 53702970, compound

Product 1

HCID 54281668HCID 54281668, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 3-(4-aminobenzylidene)-7-azaoxindol (2.373 g, 10 mmol) in pyridine (10 ml) was added gradually mesylchloride (1.146 g, 10 mmol) at 0°-5° C. under cooling. The reaction mixture was stirred for about 5 h at 0°-5° C. and then for 15 h at room temperature. The mixture was poured onto an ice-water mixture, the precipitate filtered off, the residue washed thoroughly with water and then chromatographed on silica gel using CHC3 -MeOH mixtures as eluant. Thus pure title compound was obtained in about 70% yield.

Workup

  1. temperatureunder cooling
  2. waitfor 15 h at room temperature
  3. filtrationthe precipitate filtered off
  4. washthe residue washed thoroughly with water
  5. customchromatographed on silica gel using CHC3 -MeOH mixtures as eluant

Sources & evidence

ORD record
ord-f29fa62309b04125b4c9ff315c75ce30
Source dataset
uspto-grants-1998_02
Patent number
US05719135

Reaction notes

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