Sulfuric acid magnesium salt (1:1) → methyl 3-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]benzoate

HRID 64449

Reaktionsgleichung

Reaktionsgleichung von HRID 64449
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15].S([O-])([O-])(=O)=O.[Mg+2]>ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[C:14]([S@@:17](/[N:19]=[CH:1]/[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:18])([CH3:16])([CH3:15])[CH3:13]

Komponenten

6

Edukt 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 639145Methyl 3-formylbenzoateHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Produkt 1

HCID 90072367methyl 3-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]benzoateAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of 3.0 g of methyl 3-formylbenzoate, 2.5 g of (S)-2-methyl-2-propanesulfinamide, 250 mg of pyridinium paratoluene sulfonate, and 11 g of magnesium sulfate in 50 ml of dichloromethane was stirred overnight. The reaction mixture was filtered over Celite and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 3.0 g of methyl 3-[(E)-{[(S)-tert-butylsulfinyl]imino}methyl]benzoate.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered over Celite
  2. customthe solvent was then evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ae2adc3ef3c44339aeffce4f7d770d98
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447090B2

Verknüpfte Notizen

Wird geladen…