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

HRID 2051775

Reaction equation

HRID 2051775 reaction equation
[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

Participants

5

Reactant 2

HCID 27609282-(chloromethyl)-4,5-dihydro-1H-imidazole hydrochlorideHCID 1785277551H-benzo[f]benzimidazole-2-thiol

Product 1

HCID 705692132-[(2-Imidazoline-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazoldihydrochlorideYield 58.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4c0801f701f74bbb9906b79febf8f3e0
Source dataset
uspto-grants-1980_01
Patent number
US04182766

Linked notes

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