Methanol → Deximafen

HRID 1658275

Reaktionsgleichung

Reaktionsgleichung von HRID 1658275
CO.C(C(C(C(O)=O)O)O)(O)=O.[C:13]1([CH:19]2[N:23]3[CH2:24][CH2:25][NH:26][C:22]3=[N:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[C:13]1([CH:19]2[N:23]3[CH2:24][CH2:25][NH:26][C:22]3=[N:21][CH2:20]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 21529050(-)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]imidazole (-)-tartrate

Produkt 1

HCID 163316Deximafen

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 10.7 parts of (±)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]imidazole in 20 parts of methanol is added a warm solution of 8.6 parts of (+)-tartaric acid in 20 parts of methanol. The whole is diluted with 80 parts of acetone and the product is allowed to crystallize. The precipitated fraction is filtered off [about 5.6 parts of crude (+)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]-imidazole (+)-tartrate - α(1% MeOH): +87.3°]and set aside. The filtrate is evaporated in vacuo. The residue is dissolved in water and the free base is liberated. It is extracted with chloroform and the latter is dried and evaporated. The residue is dissolved in 28 parts of methanol and to this solution is added a warm solution of 5.7 parts of (-)-tartaric acid in 60 parts of methanol. The product is allowed to crystallize. It is filtered off and recrystallized from a mixture of 8 parts of methanol and 16 parts of acetone till a constant rotation, yielding about 4.3 parts of (-)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]imidazole(-)-tartrate; α(1% MeOH): -89.97°. A sample of 4.2 parts of (-)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]imidazole(-)-tartrate is dissolved in water and the free base is liberated. After extraction with chloroform, the latter is dried and evaporated. The residue is crystallized from acetone, yielding about 0.7 parts of (-)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]-imidazole; m.p. 153.2°C.; α(1% MeOH): -211.49°. The free base together with the residue of the evaporated mother-liquor is converted into the hydrochloride salt yielding about 1.9 parts of (-)-2,3,5,6-tetrahydro-5phenyl-1H-imidazo[1,2-a]-imidazole hydrochloride; m.p. 277.1°C.; α(1% MeOH): -115.79°.

Aufarbeitung

  1. custom-89.97°
  2. extractionAfter extraction with chloroform
  3. customthe latter is dried
  4. customevaporated
  5. customThe residue is crystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-6c3630787cdb4f1abb9a15407a913d03
Quelldatensatz
uspto-grants-1976_06
Patentnummer
US03963718

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