2-(chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride → 2-[(2-Imidazoline-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazoldihydrochloride

HRID 2051775

Reaktionsgleichung

Reaktionsgleichung von HRID 2051775
[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][CH2:20][CH2:21][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 27609282-(chloromethyl)-4,5-dihydro-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 of 1H-Naphth[2,3-d]imidazole-2-thiol and 8.0 g of 2-chloromethylimidazoline-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 suctioned filtered, washed well with toluene, and crystallised 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]imidazol-dihydrochloride having an m.p. of 227°-228° were obtained.

Aufarbeitung

  1. filtrationThe residue was suctioned filtered
  2. washwashed well with toluene
  3. customcrystallised from 700 ml of methanol, with the addition of 300 ml of ether

Quellen und Nachweise

ORD-Eintrag
ord-4c0801f701f74bbb9906b79febf8f3e0
Quelldatensatz
uspto-grants-1980_01
Patentnummer
US04182766

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