Acetone → Methyl 2-[2-Hydroxy-3-[N-[2-[N-(4-methylphenylsulfonyl)amino]ethyl]amino]propoxy]benzoate Oxalate

HRID 2308966

Reaktionsgleichung

Reaktionsgleichung von HRID 2308966
[NH2:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[O:15]1[CH2:29][CH:16]1[CH2:17][O:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32].CC(C)=O>CO>[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32].[OH:15][CH:16]([CH2:29][NH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH2:17][O:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 971Oxalic AcidHCID 279510Methyl 2-(oxiran-2-ylmethoxy)benzoateHCID 301318N-(2-Aminoethyl)-4-methylbenzenesulfonamide

Produkt 1

HCID 13732868Methyl 2-[2-Hydroxy-3-[N-[2-[N-(4-methylphenylsulfonyl)amino]ethyl]amino]propoxy]benzoate Oxalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 2.15 of N-(2-aminoethyl)-p-toluenesulfonamide (0.1 mole) and 2.08 g of methyl 2-(2,3-epoxypropoxy)benzoate (0.01 mole) in 100 ml of methanol was stored at 25° C. for 4 hours. The methanol was then removed under reduced pressure, leaving an oil (NMR indicated only mono-alkylated product). The oil was then dissolved in 50 ml of methanol and an equimolar quantity of oxalic acid was added to the solution. 50 Ml of acetone was added, and the product crystallized upon refrigeration. The product was recrystallized from acetone/methanol (1:1) to yield 1.4 g of product which had a melting point of 165°-166° C. The elemental analysis (CHN) and NMR spectrum were consistent with the assigned structure.

Aufarbeitung

  1. customThe methanol was then removed under reduced pressure
  2. customleaving an oil (NMR
  3. customthe product crystallized upon refrigeration
  4. customThe product was recrystallized from acetone/methanol (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-9a56a270cf6c40819de273747a148323
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04692446

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