4-Toluenesulfonyl chloride → HCID 22323693, Verbindung

HRID 1531450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531450
O[CH2:2][CH2:3][N:4]([S:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][CH2:6][CH2:7][OH:8].[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>N1C=CC=CC=1.C(Cl)Cl>[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35]([CH2:2][CH2:3][N:4]([S:9][C:10]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:5][CH2:6][CH2:7][O:8][S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=2)(=[O:37])=[O:36])(=[O:37])=[O:36])=[CH:31][CH:30]=1

Komponenten

5

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 22323650HCID 22323650, Verbindung

Produkt 1

HCID 22323693HCID 22323693, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-(2-hydroxyethyl)-N-tritylsulfenyl-3-amino-1-propanol (5.0 g, 12.64 mmol) is dissolved in pyridine (100 mL) and cooled to 0° C. p-Toluensufonylchloride (2.65 g, 13.9 mmol) is dissolve in CH2Cl2 (50 mL) and added to the reaction mixture at 0° C. via dropping funnel. The reaction is monitored by TLC to completion. The reaction mixture is concentrated in vacuo and the resultant residue is dissolved in EtOAc and washed with H2O (3×50 mL) and brine (2×50 mL) The EtOAc is dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography using EtOAc/hexanes as eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound.

Aufarbeitung

  1. additionadded to the reaction mixture at 0° C.
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. dissolutionthe resultant residue is dissolved in EtOAc
  4. washwashed with H2O (3×50 mL) and brine (2×50 mL) The EtOAc
  5. dry with materialis dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-267f6946d39a4d99937f4445d8581899
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06197965B1

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