Water → 3,4-Dihydro-2-isoprenyloxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole

HRID 1164391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1164391
[OH:1][CH2:2][CH:3]1[S:15][C:7]2=[N:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:6]2[CH2:5][CH2:4]1.[H-].[Na+].[CH:18](Br)=[CH:19][C:20](=[CH2:22])[CH3:21].O>O1CCCC1>[CH:18]([O:1][CH2:2][CH:3]1[S:15][C:7]2=[N:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:6]2[CH2:5][CH2:4]1)=[CH:19][C:20](=[CH2:21])[CH3:22]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 128523233,4-dihydro-2-hydroxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazoleHCID 53976308Bromoisoprene

Produkt 1

HCID 867387543,4-Dihydro-2-isoprenyloxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazoleAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of one gram of 3,4-dihydro-2-hydroxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole in dry tetrahydrofuran (20 ml) was treated with 0.5 g of 50% sodium hydride containing mineral oil at 0° C. under stirring. The mixture was stirred for 1 hr, then one gram of isoprenylbromide was added, and the stirring was continued for three hours at room temperature. The reaction mixture was condensed under reduced pressure. The residue was added with water and then extracted with chloroform, and dried over anhydrous magnesium sulfate. Chloroform was evaporated under reduced pressure. The residue was chromatographed on silica gel and eluted with chloroform to obtain 0.42 g (yield: 30%) of the intended product, m.p. 56°-60° C.;

Aufarbeitung

  1. stirringThe mixture was stirred for 1 hr
  2. customcondensed under reduced pressure
  3. extractionextracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customChloroform was evaporated under reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washeluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-4dda105db4424b568af4b12be1abd273
Quelldatensatz
uspto-grants-1983_01
Patentnummer
US04369309

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