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

HRID 1003327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003327
[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-5220fa50632a4df582ac77cb5f1bfcbd
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046203

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