Propylamine → 2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonic acid propylamide

HRID 539499

Reaction equation

HRID 539499 reaction equation
[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[CH:8]=2)[NH:3]1.[Na].[NH:17]1C2[C:22](=CC(S(O)(=O)=O)=CC=2)[C:20](=O)[C:18]1=O.O=P(Cl)(Cl)Cl.CCN(C(C)C)C(C)C.C(N)CC>C1COCC1.C(OCC)(=O)C>[CH2:18]([NH:17][S:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[C:10]2=[O:11])(=[O:14])=[O:13])[CH2:20][CH3:22]

Participants

9

Reactant 6

HCID 7852PropylamineHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 817492,3-Dioxo-5-indolinesulfonic acidHCID 5360545SodiumHCID 159089472,3-Dioxoindoline-5-sulfonyl chloride

Product 1

HCID 112771782,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonic acid propylamideYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonyl chloride (0.10 g, 0.41 mmol), prepared by the reaction of the sodium salt of 5-isatinsulfonic acid with POCl3, was dissolved in 5 mL THF. This solution was cooled in an ice bath and DIEA (0.14 mL, 2.0 eq) was added slowly, followed by n-propylamine (35 uL, 1.0 eq). Stirring was continued for 40 min and the solution was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2SO4 and the solvent was removed by evaporation. The residue was purified by SiO2 chromatography to give the title compound (65 mg, 60%).

Workup

  1. temperatureThis solution was cooled in an ice bath
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed by evaporation
  5. customThe residue was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-01f3a577d6764d599cdd70d717ac8127
Source dataset
uspto-grants-2014_10
Patent number
US08871718B2

Linked notes

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