Potassium Hydroxide → 2-(3-Chloropropylthio)-5-nitrobenzenamine

HRID 50960

Reaktionsgleichung

Reaktionsgleichung von HRID 50960
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[Cl:12][CH2:13][CH2:14][CH2:15][SH:16].[OH-].[K+]>COCCOC>[Cl:12][CH2:13][CH2:14][CH2:15][S:16][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[NH2:1]

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 677852-Fluoro-5-nitroanilineHCID 871343-Chloropropanethiol

Produkt 1

HCID 227355412-(3-Chloropropylthio)-5-nitrobenzenamineAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

2-Amino-4-nitro-fluorbenzene (500 mg, 3.2 mmol), 3-chloro-1 propanethiol (354 mg, 3.2 mmol), and potassium hydroxide (269 mg, 4.8 mmol) were mixed together in ethylene glycol dimethyl ether (6.4 mL) and heated at reflux for 72 hours. The reaction was filtered and the filtercake washed with chloroform. The filtrate was concentrated and purified by flash column chromatography on 10 g if silica gel and eluted with 3% methanol in chloroform to give 2-[(3-chloropropyl)sulfanyl]-5-nitrophenylamine (130 mg, 17%). 1H NMR (CDCl3, 300 MHz): δ7.49-7.48 (m, 2H), 7.38 (dd, 1H, J=7.7 Hz, J=7.7 Hz), 4.55 (s-broad, 2H), 3.64 (t, 2H, J=6.2 Hz), 3.03 (t, 2H, J=7 Hz), 2.00 (q, 2H, J=7 Hz) ppm. Mass Spec (ESI):264 (base M+H).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 72 hours
  3. filtrationThe reaction was filtered
  4. washthe filtercake washed with chloroform
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash column chromatography on 10 g if silica gel
  7. washeluted with 3% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-27d01dcecd164d1e8069869a5cb0d0a0
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713471B1

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