4-Toluenesulfonyl chloride → HCID 18918306, Verbindung

HRID 1290472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1290472
Cl.[C:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)(=[O:4])[CH3:3].C(N(CC)CC)C.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>ClCCl>[C:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:10][S:27]([C:24]2[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][CH:23]=2)(=[O:29])=[O:28])=[CH:7][CH:6]=1)(=[O:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 124353931-[4-(Aminomethyl)phenyl]ethan-1-one hydrochloride

Produkt 1

HCID 18918306HCID 18918306, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

To a stirred suspension under argon of 4-acetylbenzylamine hydrochloride (700 mg) in dichloromethane (20 ml) was added triethylamine (1.15 ml) and stirring continued for 15 minutes. The mixture was cooled to 4° C., then 4-methylphenylsulphonyl chloride (790 mg) in dichloromethanie (5 ml) added dropwise over 30 minutes. The reaction mixture was stirred for 18 hours at ambient temperature, then diluted with further dichloromethane (50 ml), washed with water, dried (MgSO4) and evaporated. Trituration of the residue gave N-([4-acetylphenyl]methyl)-4-methylphenysulphonamide (A), 1.02 g., as an off-white solid: m.p. 125°-128° C.; NMR (d6DMSO) δ 8.13(1H,t), 7.86(2H,d), 7.68(2H,d), 7.37(4H,dd), 4.03(2H,d), 2.55(3H,s), 2.39(3H,s); m/e 304(M+H)+.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 18 hours at ambient temperature
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-634b379be85c4761b51ce4276bdcde38
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750754

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