3,4-dihydro-2-methoxycarbonyl-2H-(1,3)-thiazino-[3,2-a]benzimidazole → 3,4-dihydro-2-hydroxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole

HRID 544356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544356
C[O:2][C:3]([CH:5]1[S:17][C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:2][CH2:3][CH:5]1[S:17][C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[CH2:7][CH2:6]1

Komponenten

4

Edukt 2

HCID 128512483,4-dihydro-2-methoxycarbonyl-2H-(1,3)-thiazino-[3,2-a]benzimidazoleHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 128523233,4-dihydro-2-hydroxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazoleAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2.48 g (10 m mole) of 3,4-dihydro-2-methoxycarbonyl-2H-(1,3)-thiazino-[3,2-a]benzimidazole in dry tetrahydrofuran (50 ml) was added dropwise 0.5 g of lithium aluminum hydride devided in small pieces, with stirring under ice cooling condition. After thirty minutes, the resultant complex was decomposed by the addition of hydrated tetrahydro furan and subjected to filtration. Subsequent to drying the filtrate over anhydrous magnesium sulfate, tetrahydrofuran was evaporated under reduced pressure. The residue was chromatographed on silica gel and eluted with chloroform to obtain 1.2 g (yield: 54.5%) of the intended product, m.p. 112°-113° C.; IR νmaxKBr cm-1 : 3500-3000, 1430; Anal. Calcd. for C11H12N2OS: C, 59.98; H, 5.49; N, 12.72; S, 14.55; Found: C, 59.71; H, 5.61, N, 12.99; S, 14.15.

Aufarbeitung

  1. waitAfter thirty minutes
  2. filtrationsubjected to filtration
  3. dry with materialSubsequent to drying the filtrate over anhydrous magnesium sulfate, tetrahydrofuran
  4. customwas evaporated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-52f4715c93914fe7901b4f77d0ae34c5
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04450109

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