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D-Glucosamine → 1-(1,2,3,4-Tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione

HRID 863076
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 863076
[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)=[C:2]=[S:3].O[CH:15]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H:16]1[NH2:17]>C(O)(=O)C>[CH2:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:12][CH2:13][CH:4]1[N:1]1[CH:15]=[CH:16][NH:17][C:2]1=[S:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 439213D-GlucosamineHCID 196994682-Isothiocyanato-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 196993691-(1,2,3,4-Tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thioneAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-isothiocyano-1,2,3,4-tetrahydronaphthalene (1.89 g, 10 mmol), prepared as in Example 10, and D-(+)-glucosamine (1.78 g, 10 mmol) was stirred at 90° C. until homogenous and then 0.8 mL of acetic acid was added. The mixture was stirred at 90° C. for 30 minutes and then cooled. The solvents were removed by rotary evaporation and the residue was co-evaporated with toluene (2×25 mL). The residue was dissolved in acetic acid and heated at 90° to 100° C. for 30 minutes. The mixture was cooled and triturated with acetone giving a crystalline material. The material was isolated by filtration and the filter residue washed with acetone. Drying gave 4-(1R,2R,3S,4)-tetrahydroxybut-1-yl)-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (1.48 g, 4.23 mmol).

Aufarbeitung

  1. additionwas added
  2. temperaturecooled
  3. customThe solvents were removed by rotary evaporation
  4. dissolutionThe residue was dissolved in acetic acid
  5. temperatureheated at 90° to 100° C. for 30 minutes
  6. temperatureThe mixture was cooled
  7. customtriturated with acetone giving a crystalline material
  8. customThe material was isolated by filtration
  9. washthe filter residue washed with acetone
  10. customDrying

Quellen und Nachweise

ORD-Eintrag
ord-fdd64a4665004337b1d06b7c44ed236c
Quelldatensatz
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05719280

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