Triethylamine → HCID 13884647, Verbindung

HRID 1583510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1583510
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(N(CC)CC)C>ClCCl>[CH3:24][S:25]([O:11][CH2:10][CH2:9][S:8][C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:27])=[O:26]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2793702-(tritylsulfanyl)ethanol

Produkt 1

HCID 13884647HCID 13884647, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(triphenylmethylthio)ethanol (2.66 g, 8.30 mmol) in cold (0° C.) dichloromethane (39 mL) kept under a nitrogen atmosphere was added methanesulfonyl chloride (0.704 mL, 9.10 mmol); the resulting mixture was treated dropwise (15 min) with triethylamine (1.34 mL, 9.6 mmol). After stirring for 15 min, the cooling bath was removed and the reaction mixture was stirred for 7 h then washed successively with water (10 mL), 0.5N citric acid (10 mL), water (10 mL), saturated sodium bicarbonate and water. The organic extracts were dried (MgSO4 -MgO) and concentrated under reduced pressure to a thick syrup which crystallized on standing. Trituration of the crystals in ether afforded white solid 2.1 g (63%) mp 95°-8° C.; ir (KBr) νmax : 1580, 1565 (phenyl), 1350, 1175, 1165 cm-1 (sulfonate); 1Hmr (CDCl3): 251 (2H, t, J=6.6 Hz, CH2S), 3.07 (3H, s, CH3SO3), 3.87 (2H, t, J=6.6 Hz, CH2O), 7.34 (15H, m, phenyl).

Aufarbeitung

  1. customthe cooling bath was removed
  2. stirringthe reaction mixture was stirred for 7 h
  3. washthen washed successively with water (10 mL), 0.5N citric acid (10 mL), water (10 mL), saturated sodium bicarbonate and water
  4. dry with materialThe organic extracts were dried (MgSO4 -MgO)
  5. concentrationconcentrated under reduced pressure to a thick syrup which
  6. customcrystallized

Quellen und Nachweise

ORD-Eintrag
ord-839ebe6e2b1c4b2eac59325d480c005b
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04552696

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