p-Toluenesulfonic acid → 1-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4,5-di-hydro-imidazole dihydrochloride

HRID 357621

Reaktionsgleichung

Reaktionsgleichung von HRID 357621
[ClH:1].[C:2]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][C:9]2=O)(=[NH:4])[NH2:3].Cl.[NH2:16][N:17]1[CH2:21][CH2:20][N:19]=[C:18]1[NH2:22].CC1C=CC(S(O)(=O)=O)=CC=1.C=CC1C=CC=CC=1.C(C1C=CC=CC=1C=C)=C>O>[ClH:1].[ClH:1].[C:2]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][C:9]2=[N:16][N:17]1[CH2:21][CH2:20][N:19]=[C:18]1[NH2:22])(=[NH:4])[NH2:3]

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 174664Divinylbenzene-styreneHCID 189379401,2-Diamino-4,5-dihydro-imidazole hydrochlorideHCID 189379431-Oxo-2,3-dihydro-1H-indene-4-carboximidamide--hydrogen chloride (1/1)

Produkt 1

HCID 699043851-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4,5-di-hydro-imidazole dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 0.24 g (0.001 mol) of 4-amidino-2,3-dihydro-1H-inden-1-one hydrochloride and 0.136 g (0.001 mol) of 1,2-diamino-4,5-dihydro-imidazole hydrochloride [m.p. 245°-246° C., prepared from the corresponding p-toluenesulfonate salt, see EP 0 327 919, Example 12, by ion exchange on ®Amberlite IRA-400 (anion exchanger based on a styrene/divinylbenzene polymer with quaternary ammonium groups in the Cl- form; Fluka, Buchs, Switzerland)] in 3 ml of water is left to stand at room temperature for 18 hours. The product that has crystallized out is filtered off with suction and recrystallized from water, yielding the title compound (monohydrate), m.p. 280° C. (decomp.), 1 H-NMR (DMSO/D2O): δ=8.17 (d, 1H); 7.66 (d, 1H); 7.54 (t, 1H); 4.18 (t, 2H); 3.70 (t, 2H); 3.25 (m, 2H); 3.13 (m, 2H).

Aufarbeitung

  1. customThe product that has crystallized out
  2. filtrationis filtered off with suction
  3. customrecrystallized from water

Quellen und Nachweise

ORD-Eintrag
ord-97b2d694d9664a8eaae5ae32eeeca138
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840911

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