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1,4-Dioxane → 2-(1-Methyl-1H-imidazol-4-yl)ethanamine bis(4-methylbenzenesulfonate)

HRID 1014962
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1014962
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][N+:13]1[CH:21]=[C:20]2[N:15](C(=O)[NH:17][CH2:18][CH2:19]2)[CH:14]=1.O.[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1.O1CCOCC1>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH3:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:29][CH:30]=1.[CH3:12][N:13]1[CH:21]=[C:20]([CH2:19][CH2:18][NH2:17])[N:15]=[CH:14]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 312751,4-DioxaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86622930HCID 86622930, Verbindung

Produkt 1

HCID 862548242-(1-Methyl-1H-imidazol-4-yl)ethanamine bis(4-methylbenzenesulfonate)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-methyl-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-2-ium 4-methylbenzenesulfonate (625.1 g), 4-methylbenzenesulfonic acid hydrate (406.6 g), 1,4-dioxan (9.38 litres) and water (625 ml) was heated at reflux (ca. 90° C.) for 2.5 h. when the reaction was complete by nmr. The reaction mixture was concentrated by distillation at atmospheric pressure collecting 7.03 litres. The concentrate was allowed to cool to ca. 77° C., and IMS-G (1.56 litres) was added. The resulting bright solution was allowed to cool and was seeded with [2-(1-methyl-1H-imidazol-4-yl)ethyl]amine bis(4-methylbenzenesulfonate) (0.625 g) at ca. 54° C. The suspension was allowed to cool to ca. 22° C. and aged for 40 min. The solid was filtered off and washed successively with 1,4-dioxan-IMS (3:1, 1.25 litres), and then 1,4-dioxan (2×1.25 litres), pulled dry and dried in vacuo at ca. 50° C. to yield the title compound, 866.3 g.

Aufarbeitung

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrated by distillation at atmospheric pressure
  3. customcollecting 7.03 litres
  4. temperatureto cool to ca. 77° C.
  5. additionIMS-G (1.56 litres) was added
  6. temperatureto cool
  7. customwas seeded with [2-(1-methyl-1H-imidazol-4-yl)ethyl]amine bis(4-methylbenzenesulfonate) (0.625 g) at ca. 54° C
  8. temperatureto cool to ca. 22° C. and aged for 40 min
  9. filtrationThe solid was filtered off
  10. washwashed successively with 1,4-dioxan-IMS (3:1, 1.25 litres)
  11. dry with material1,4-dioxan (2×1.25 litres), pulled dry
  12. customdried in vacuo at ca. 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-1ae5a96a6cf441db843f5f83e22e5071
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07985740B2

Notizen zur Reaktion

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