4-Chlorobenzenesulfonyl chloride → 4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide

HRID 1011551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1011551
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1([CH2:19][OH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2([CH2:19][OH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 409153(1-Aminocyclohexyl)methanol

Produkt 1

HCID 210787144-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamideAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Chlorobenzenesulfonyl chloride (6.92 g, 32.8 mmol) was added to a solution of (1-aminocyclohexyl)methanol (prepared according to Helv. Chirp. Acta, 87:90-105 (2004)) (3.53 g, 27.3 mmol) and triethylamine (4.6 mL, 32.8 mmol) in 100 mL tetrahydrofuran at room temperature. The reaction was stirred overnight and concentrated. The residue was taken up in a mixture of 100 mL ethyl acetate and 100 mL brine. The organic layer was separated, dried over sodium sulfate, and purified by flash chromatography on 120 g silica gel with 20 to 100% ethyl acetate in hexane to yield 4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide (6.07 g, 73%). 1H NMR (400 MHz, CDCl3) δ ppm 7.85-7.86 (1H, m), 7.81-7.84 (1H, m), 7.47-7.49 (1H, m), 7.44-7.46 (1H, m), 4.61 (1H, s), 3.60 (2H, d, J=5.54 Hz), 2.25 (1H, t, J=5.92 Hz), 1.57-1.69 (2H, m), 1.22-1.45 (8H, m). LC/MS R.T.=2.39 min; [M+H]+=304.03; [M+Na]+=326.05; [M−H]−=301.98.

Aufarbeitung

  1. concentrationconcentrated
  2. additionThe residue was taken up in a mixture of 100 mL ethyl acetate and 100 mL brine
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. custompurified by flash chromatography on 120 g silica gel with 20 to 100% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-2397997a49be4845b8e6fd22bf96a569
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977362B2

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