Methylamine → N-methyl-2-oxoindoline-5-sulfonamide

HRID 1386356Notes

Reaction equation

HRID 1386356 reaction equation
[CH3:1][NH2:2].Cl[S:4]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10]2)(=[O:6])=[O:5]>C(Cl)(Cl)Cl.C(Cl)Cl.C(O)C>[CH3:1][NH:2][S:4]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10]2)(=[O:6])=[O:5]

Participants

6

Reactant 2

HCID 6329MethylamineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 10176909N-methyl-2-oxoindoline-5-sulfonamideYield 90%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Methylamine (2.7 ml of a 2.9M solution in chloroform) was added to a suspension of 5-chlorosulphonyloxindole (900 mg, 3.9 mmol), (prepared as described for the starting material in Example 60), in a mixture of methylene chloride (20 ml) and ethanol (20 ml). The mixture was stirred for 15 minutes at ambient temperature, the volatiles were removed by evaporation. The solid residue was suspended in water, collected by filtration, washed with water, ether, and dried under vacuum over phosphorus pentoxide to give 5-methylaminosulphonyloxindole (880 mg, 90%).

Workup

  1. custom(prepared
  2. customthe volatiles were removed by evaporation
  3. filtrationcollected by filtration
  4. washwashed with water, ether
  5. dry with materialdried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-5111b332df3d40fca1f2fb39dcd6f1e7
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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