(2-Chloro-6-nitrophenyl)(3-chloropropyl)sulfane → 3-Chloro-2-[(3-chloropropyl)sulfanyl]aniline

HRID 50964

Reaktionsgleichung

Reaktionsgleichung von HRID 50964
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[S:11][CH2:12][CH2:13][CH2:14][Cl:15]>CO>[Cl:1][C:2]1[C:3]([S:11][CH2:12][CH2:13][CH2:14][Cl:15])=[C:4]([CH:5]=[CH:6][CH:7]=1)[NH2:8]

Komponenten

3

Edukt 1

HCID 22735865(2-Chloro-6-nitrophenyl)(3-chloropropyl)sulfane

Produkt 1

HCID 227355373-Chloro-2-[(3-chloropropyl)sulfanyl]anilineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The crude 1-chloro-2-[(3-chloropropyl)sulfanyl]-3-nitrobenzene was dissolved in MeOH (150 mL) and degassed with N2. Palladium hydroxide (1.8 g) was added in four portions to this solution in a Parr appararus. The resulting heterogeneous solution was shaken under hydrogenation conditions (55 psi) at room temp for 18 h. The catalyst was removed via filtration in the same manner as above and the filtrate was concentrated in vacuo. to afford 3-chloro-2-[(3-chloropropyl)sulfanyl]aniline (9.94 g, 93%) as a dark oil: 1H NMR (CHCl3, 300 MHz) δ7.03 (t, 1H, J=8.1 Hz), 6.82 (t, 1H, J=8.1 Hz), 6.63 (t, 1H, J=8.0 Hz), 4.62 (br s, 1H), 3.68 (t, 2H, J=6.4 Hz), 2.92 (t, 2H, J=6.9 Hz), 1.98 (quintet, 2H, J=6.6 Hz) ppm.

Aufarbeitung

  1. customdegassed with N2
  2. additionPalladium hydroxide (1.8 g) was added in four portions to this solution in a Parr appararus
  3. customThe catalyst was removed via filtration in the same manner as above and the filtrate
  4. concentrationwas concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-904e74b753614e24915791cedb72e393
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713471B1

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