Methyl Isocyanate → 3-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-5-yl methylcarbamate

HRID 1003335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003335
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[C:14]3[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:13]=3[O:12][N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:20][N:21]=[C:22]=[O:23].CC(C)=O.CO.C(Cl)Cl>CCOC(C)=O.[Cu]Cl>[CH3:20][NH:21][C:22](=[O:23])[O:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][N:11]=[C:10]([NH:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[C:14]=2[CH:15]=1

Komponenten

6

Edukt 3

HCID 12228Methyl IsocyanateHCID 187964613-[[2-(4-Morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-olHCID 21584259acetone MeOH DCM

Produkt 1

HCID 187964473-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-5-yl methylcarbamateAusbeute 32,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-ol (1 g) and a catalytic amount of copper(I)chloride (0.05 g) in EtOAc (100 ml) was added methyl isocyanate (0.26 g). After 24 hours TLC (silica gel, 1:1:20 acetone/MeOH/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (1 l) and the filtrate was concentrated in vacuo. The residue was further purified by flash chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM to yield 0.4 g of the product, m.p. 135-136° C.

Aufarbeitung

  1. filtrationThe reaction was filtered through neutral alumina eluting with EtOAc (1 l)
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was further purified by flash chromatography (silica gel)
  4. washeluting with 1:1:20 acetone/MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-a26a1c2e1aef4addb163e050c577177b
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046203

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