Sodium Chloride → S-(2-aminostyryl)-S-phenyl sulfoximine

HRID 1906721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1906721
C[S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[NH:4])=[O:3].[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].C(#[N:23])C1C=CC=CC=1.[Cl-].[Na+].O1[CH2:30][CH2:29][CH2:28][CH2:27]1>CCCCCC.CCOC(C)=O.C(Cl)Cl>[NH2:23][C:14]1[CH:30]=[CH:29][CH:28]=[CH:27][C:13]=1[CH:12]=[CH:11][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[NH:4])=[O:3]

Komponenten

9

Edukt 5

HCID 5234Sodium ChlorideHCID 7505BenzonitrileHCID 8028TetrahydrofuranHCID 290021(Methylsulfonimidoyl)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 73665723S-(2-aminostyryl)-S-phenyl sulfoximineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 8.3 g (0.053 mole) of methyl phenyl sulfoximine in 400 ml of dry tetrahydrofuran at 0° C. was added 1.4M (0.13 mol) butyl lithium in hexane to obtain a clear yellow solution. 15 ml (0.172 mole) of benzonitrile were added and the mixture was stirred for 30 minutes. 100 ml of saturated sodium chloride solution were added and the organic layer was separated, dried over magnesium sulfate and evaporated to an oil. The crude oil was triturated with petrol-ether (40° C.-60° C.) and then was chromatographed over silica. Elution with CH2Cl2, then a 1--1 CH2Cl2 : EtOAc mixture yielded 8.8 g (64% yield) of pure S-(2-aminostyryl)-S-phenyl sulfoximine melting at 95°-96° C. after crystallization from ether.

Aufarbeitung

  1. customto obtain a clear yellow solution
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to an oil
  5. customThe crude oil was triturated with petrol-ether (40° C.-60° C.)
  6. customwas chromatographed over silica
  7. washElution with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-96903bbdca13479d86b3e6064c1d50c4
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04654338

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