Isopropyl isocyanate → 3-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-yl 1-methylethylcarbamate

HRID 582863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582863
[N:1]1([CH2:7][CH2:8][N:9]([CH3:20])[C:10]2[C:14]3[CH:15]=[CH:16][C:17]([OH:19])=[CH:18][C:13]=3[O:12][N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:21][CH:22]([N:24]=[C:25]=[O:26])[CH3:23].CO.C(Cl)Cl>CCOC(C)=O.[Cu]Cl>[CH3:21][CH:22]([NH:24][C:25](=[O:26])[O:19][C:17]1[CH:16]=[CH:15][C:14]2[C:10]([N:9]([CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH3:20])=[N:11][O:12][C:13]=2[CH:18]=1)[CH3:23]

Komponenten

6

Edukt 3

HCID 61277Isopropyl isocyanateHCID 21226129Dichloromethane methanolHCID 1358150583-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-ol

Produkt 1

HCID 154351373-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-yl 1-methylethylcarbamateAusbeute 41,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]-methylamino]-1,2-benzisoxazol-6-ol (2.2 g) and copper(I)chloride (0.1 g) in EtOAc (50 ml) was added 1-methylethylisocyanate (0.8 g). After 24 hours TLC (silica gel, 10% MeOH/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (3 l) and the filtrate was concentrated in vacuo. The white solid was flash chromatographed on silica gel eluting with 1% MeOH/DCM to yield 1.2 g of the product, m.p. 99-100° C.

Aufarbeitung

  1. filtrationThe reaction was filtered through neutral alumina eluting with EtOAc (3 l)
  2. concentrationthe filtrate was concentrated in vacuo
  3. customchromatographed on silica gel eluting with 1% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-f89235da09b14b26bb7a8677a8d6a3d2
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925766

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