Water → 1-(3-methylphenyl)-3-[4-(1-oxo-2,3-dihydro-1H-isoindol-4-yl)phenyl]thiourea

HRID 1247462

Reaktionsgleichung

Reaktionsgleichung von HRID 1247462
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][NH:11][C:12]3=[O:17])=[CH:4][CH:3]=1.[C:18]1([CH3:27])[CH:23]=[CH:22][CH:21]=[C:20]([N:24]=[C:25]=[S:26])[CH:19]=1.O>CN(C=O)C>[CH3:27][C:18]1[CH:19]=[C:20]([NH:24][C:25]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:9]=3[CH2:10][NH:11][C:12]4=[O:17])=[CH:6][CH:7]=2)=[S:26])[CH:21]=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 69304m-TolylisothiocyanateHCID 219075114-(4-Aminophenyl)isoindolin-1-one

Produkt 1

HCID 53298851-(3-methylphenyl)-3-[4-(1-oxo-2,3-dihydro-1H-isoindol-4-yl)phenyl]thioureaAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of Example 1D (0.1 g, 0.44 mmol) in DMF (3 mL) was treated with m-tolylisothiocyanate (0.06 mL, 0.45 mmol), stirred at room temperature overnight, then cooled to 0° C., treated with water, and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 3% methanol/dichloromethane to give 72 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 2.30 (s, 3H); 4.53 (s, 2H); 6.96 (d, J=7.12 Hz, 1H); 7.23 (t, J=7.80 Hz, 1H); 7.29 (d, J=7.80 Hz, 2H); 7.57–7.69 (m, 7H); 8.68 (s, 1H); 9.84 (s, 1H); 9.88 (s, 1H); MS (ESI(−)) m/e 372 (M−H)−.

Aufarbeitung

  1. temperaturecooled to 0° C.
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 3% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-45b1eb922cfc46a0bad5a5bf646e7a74
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129260B2

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