Hydrochloric Acid → HCID 20969407, compound

HRID 49110Notes

Reaction equation

HRID 49110 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1.Cl>ClCCl.C(OCC)(=O)C>[CH2:15]([NH:22][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7504BenzylamineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 20969407HCID 20969407, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5-chlorosulfonyl-2-oxindole (1.62 g, 7 mmol), benzylamine (0.918 mL, 8.4 mmol) and pyridine (1 mL) in dichloromethane (20 mL) was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and acidified with 1N hydrochloric acid (16 mL). The organic layer was then washed with sodium bicarbonate and brine, dried and concentrated. The residue was washed with ethanol (3 mL) and was then purified by chromatography on silica gel eluting with methanol:dichloromethane 1:9 to give 1.4 g (66%) of 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid benzylamide.

Workup

  1. washThe organic layer was then washed with sodium bicarbonate and brine
  2. customdried
  3. concentrationconcentrated
  4. washThe residue was washed with ethanol (3 mL)
  5. customwas then purified by chromatography on silica gel eluting with methanol:dichloromethane 1:9

Sources & evidence

ORD record
ord-4035448cd9454c1ab7622b551da54dd4
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

Loading…