Dimethyl Sulfide → HCID 19046449, Verbindung

HRID 1439935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1439935
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([Cl:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].ClN1C(=O)CCC1=O.[CH3:21][S:22][CH3:23].C(N(CC)CC)C>ClCCl>[C:1]([C:5]1[CH:11]=[C:10]([CH2:21][S:22][CH3:23])[C:8]([NH2:9])=[C:7]([Cl:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 5210944-(Tert-Butyl)-2-Chloroaniline

Produkt 1

HCID 19046449HCID 19046449, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

4-t-Butyl-2-chloroaniline (30 g) was dissolved in dichloromethane (1.21) and the solution was cooled to -5° C. N-chlorosuccinimide (21.7 g) was added portionwise to the vigorously stirred solution and stirring was continued for 1 h. Dimethyl sulfide (35 ml) was added to the solution (-5° C.) and stirring was continued for a further 1 h. The solution was then cooled to -65° C. and triethylamine (27 ml) was added. This solution was allowed to warm to room temperature overnight. The solution was evaporated to half volume, washed with sodium hydroxide (1N), water and brine successively. The organic solution was dried and evaporated and the residue was purified on silica using hexane to 3% ether in hexane as eluant. This afforded the product (31.2 g) as a red oil. 1H NMR (CDCl3, 250 MHz) δ 1.27 (9H, s, (CH3)3), 1.99 (3H, s, SCH3 ), 3.69 (2H, s, CH2SCH3), 4.38 (2H, br s, NH2), 6.92 (1H, d, J=2.0 Hz, ArH), 7.21 (1H, d, J=2.0 Hz, ArH). MS (CI+) m/z 244 (M+ +1, 100%).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for a further 1 h
  3. temperatureThe solution was then cooled to -65° C.
  4. temperatureto warm to room temperature overnight
  5. customThe solution was evaporated to half volume
  6. washwashed with sodium hydroxide (1N), water and brine successively
  7. customThe organic solution was dried
  8. customevaporated
  9. customthe residue was purified on silica

Quellen und Nachweise

ORD-Eintrag
ord-8ba57f399ec742878ffc403c0525a67b
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05496833

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