Potassium Iodide → 2-[6-[[(Z)-[(4-methyl-1,2,5-thiadiazol-3-yl)-phenylmethylidene]amino]oxymethyl]-2-pyridinyl]isoindole-1,3-dione

HRID 2039685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2039685
[OH:1][N:2]=[C:3]([C:10]1[C:14]([CH3:15])=[N:13][S:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:17][C:18]1[N:23]=[C:22]([N:24]2[C:32](=[O:33])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]2=[O:34])[CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O>[CH3:15][C:14]1[C:10](/[C:3](=[N:2]\[O:1][CH2:17][C:18]2[N:23]=[C:22]([N:24]3[C:25](=[O:34])[C:26]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:32]3=[O:33])[CH:21]=[CH:20][CH:19]=2)/[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[N:11][S:12][N:13]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 112323512-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dioneHCID 136351090N-hydroxy-1-(4-methyl-1,2,5-thiadiazol-3-yl)-1-phenylmethanimine

Produkt 1

HCID 873948112-[6-[[(Z)-[(4-methyl-1,2,5-thiadiazol-3-yl)-phenylmethylidene]amino]oxymethyl]-2-pyridinyl]isoindole-1,3-dioneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of N-hydroxy-1-(4-methyl-1,2,5-thiadiazol-3-yl)-1-phenylmethanimine (24.3 g, 111 mmol) in dry acetonitrile (600 mL) were added 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (36.9 g, 116 mmol), cesium carbonate (37.9 g, 116 mmol) and potassium iodide (1.84 g, 11 mmol). The reaction mixture was stirred at room temperature for 14 h, then diluted with water (200 mL) and concentrated in vacuo. The residue was extracted with ethyl acetate (2×300 mL). The combined organic layers were combined and concentrated in vacuo to afford 2-{6-[({[(Z)-(4-methyl-1,2,5-thiadiazol-3-yl)(phenyl)methylene]amino}-oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione as a red oil [49 g, yield 82%; HPLC/MS: m/z=456 (M+H); log P(HCOOH)=3.99].

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. extractionThe residue was extracted with ethyl acetate (2×300 mL)
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ed7bd2a38cd44a0ea4d6f27926ed801c
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580799B2

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