Water → 2-Chloro-5-(4-methoxy-benzoyl)-N-phenethyl-benzenesulfonamide

HRID 1810161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810161
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:18](Cl)(=[O:20])=[O:19].[CH2:22]([NH2:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:18]([NH:30][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:20])=[O:19]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1001PhenethylamineHCID 8471TriethylamineHCID 581074452-Chloro-5-(4-methoxy-benzoyl)-benzenesulfonyl chloride

Produkt 1

HCID 581074872-Chloro-5-(4-methoxy-benzoyl)-N-phenethyl-benzenesulfonamideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Chloro-5-(4-methoxy-benzoyl)-benzenesulfonyl chloride (0.2 g, 5.79 mmol) is dissolved in methylene chloride (10 mL). Phenethylamine (0.077 g, 6.36 mmol) is added, followed by the addition of triethylamine (0.146 g, 14.5 mmol). The reaction mixture is stirred for 2 h at room temperature. Water is added, and the mixture extracted with methylene chloride. The solvent is removed and the mixture is purified by flash column chromatography, using 50% of ethyl acetate-hexane as an eluent. The product is obtained as a colorless oil (0.13 g, 52% yield). 1H NMR (CDCl3): δ 8.4 (m, 1H), 7.90 (m, 1H), 7.50 (d, J=8 Hz, 2H), 7.28 (m, 3H), 7.00 (d, J=8 Hz, 2H), 7.17 (m, 2H), 4.97 (m, 1H), 3.91 (s, 3H), 3.20 (m, 2H), 2.80 (m, 2H). Analytics calculated for C22H20ClNO4S: C, 61.46; H, 4.69; N, 3.26. Found: C, 61.20; H, 4.95; N, 3.10. MS (m/z): 430.0 (M+1).

Aufarbeitung

  1. extractionthe mixture extracted with methylene chloride
  2. customThe solvent is removed
  3. customthe mixture is purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2df8346f45604d4789874910c685f6ee
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362063B2

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