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

HRID 1689611

反応式

HRID 1689611 の反応式
[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]

参加物

9

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-741ab8bdf9794660af893b58005f28d3
出典データセット
uspto-grants-2012_04
特許番号
US08153593B2

関連ノート

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