2-(Chloromethyl)-1H-imidazole hydrochloride → 2-[(2-Imidazoline-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazoldihydrochloride

HRID 1413113

Reaktionsgleichung

Reaktionsgleichung von HRID 1413113
[NH:1]1[C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][C:4]=2[N:3]=[C:2]1[SH:14])[CH:11]=[CH:10][CH:9]=[CH:8]3.[ClH:15].[Cl:16][CH2:17][C:18]1[NH:19][CH:20]=[CH:21][N:22]=1>CN(C)C=O.C1(C)C=CC=CC=1>[ClH:16].[ClH:15].[NH:22]1[CH2:21][CH2:20][N:19]=[C:18]1[CH2:17][S:14][C:2]1[NH:3][C:4]2[CH:13]=[C:12]3[C:7](=[CH:6][C:5]=2[N:1]=1)[CH:8]=[CH:9][CH:10]=[CH:11]3

Komponenten

5

Edukt 2

HCID 27609292-(Chloromethyl)-1H-imidazole hydrochlorideHCID 1785277551H-benzo[f]benzimidazole-2-thiol

Produkt 1

HCID 705692132-[(2-Imidazoline-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazoldihydrochlorideAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

10.0 g 1H-Naphth[2,3-d]imidazole-2-thiol and 8.0 g of 2-chloromethylimidazole-hydrochloride were heated for 3 hours at 90° in 50 ml of dimethylformamide. The reaction mixture was cooled to room temperature and then diluted with 200 ml of toluene. The residue was suction filtered, washed well with toluene, and crystallized from 700 ml of methanol, with the addition of 300 ml of ether. 10.3 g of 2-[(2-Imidazoline-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazoldihydrochloride having an m.p. of 227°-228° were obtained.

Aufarbeitung

  1. filtrationfiltered
  2. washwashed well with toluene
  3. customcrystallized from 700 ml of methanol, with the addition of 300 ml of ether

Quellen und Nachweise

ORD-Eintrag
ord-29872955b0284e9e861e4e0a704ba025
Quelldatensatz
uspto-grants-1981_02
Patentnummer
US04248880

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