HCID 19046449, Verbindung → HCID 19046432, Verbindung

HRID 1757235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1757235
[C:1]([C:5]1[CH:11]=[C:10]([CH2:12]SC)[C:8]([NH2:9])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[CH:11]=[C:10]([CH3:12])[C:8]([NH2:9])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 19046449HCID 19046449, Verbindung

Produkt 1

HCID 19046432HCID 19046432, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

4-t-Butyl-2-chloro-6-(methylthiomethyl)aniline (1.3 g) was dissolved in methanol (50 ml) and Raney nickel (prewashed to pH 7) was added portionwise until t.l.c. indicated all starting material had reacted (ether-hexane, 1:10). The Raney nickel was removed by filtration through celite and the filtrate was evaporated. The residue was dissolved in ether and washed with brine, dried (MgSO4) and evaporated. The residue was purified on silica using hexane--5% ether in hexane as eluant to afford the product as a yellow liquid. 1H NMR (360 MHz, CDCl3) δ1.26 (9H, s, (CH3)3), 2.19 (3H, s, CH3), 3.97 (2H, s, NH2), 6.97 (1H, d, J=2.0 Hz, ArH), 7.14 (1H, d, J=2.0 Hz, ArH).

Aufarbeitung

  1. customThe Raney nickel was removed by filtration through celite
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified on silica

Quellen und Nachweise

ORD-Eintrag
ord-0dc1f02fd7d14e34a09343794444abe7
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05444074

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