Methanesulfonyl chloride → HCID 70128698, compound

HRID 1376791Notes

Reaction equation

HRID 1376791 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1.[S:22](Cl)([CH3:25])(=[O:24])=[O:23]>N1C=CC=CC=1>[S:22]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)([CH3:25])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 53909416HCID 53909416, compound

Product 1

HCID 70128698HCID 70128698, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 5-amino-3-[(7-azaindol-3-yl) methylene]-2-oxindole (2.773 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 CHCl3 --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

Sources & evidence

ORD record
ord-781f23e8627f4232a0c77648452765db
Source dataset
uspto-grants-1997_09
Patent number
US05663346

Reaction notes

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