Potassium Carbonate → 4-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide

HRID 472378

Reaktionsgleichung

Reaktionsgleichung von HRID 472378
[NH:1]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][CH:17]=1>CC(C)=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:1]2[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]2)=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 68528p-Bromobenzyl chlorideHCID 6484228Thiomorpholine 1,1-dioxide

Produkt 1

HCID 523254684-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a well stirred suspension of thiomorpholine 1,1-dioxide (0.36 g, 2.7 mmol) and potassium carbonate (0.37 g, 2.7 mmol) in acetone (5 mL) was added 1-bromo-4-chloromethyl-benzene (0.50 g, 2.4 mmol). The mixture was stirred for 48 hours at room temperature. The mixture was filtered and the volatiles were evaporated. The residue was suspended in ether (100 mL), filtered and evaporated to a solid. The material was purified via chromatography utilizing an ISCO automated purification apparatus (24 g silica gel column 10%→100% ethyl acetate in hexane). 4-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide was isolated as a white solid (0.72 g, 97%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.47 (d, J=7.6 Hz, 2H), 7.19 (d, J=7.7 Hz, 2H), 3.60 (s, 2H), 3.08-2.94 (m, 8H). MS=304, 306 (MH)+.

Aufarbeitung

  1. stirringThe mixture was stirred for 48 hours at room temperature
  2. filtrationThe mixture was filtered
  3. customthe volatiles were evaporated
  4. filtrationfiltered
  5. customevaporated to a solid
  6. customThe material was purified via chromatography
  7. custompurification apparatus (24 g silica gel column 10%→100% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d31aa3f94bd74546ac9e0316d120c040
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633173B2

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