1,2-Dimethylbenzimidazole → 1,1'-{disulfanediylbis[ethane-2,1-diylimino(2-oxoethane-2,1-diyl)]}bis(2,3-dimethyl-1H-benzimidazol-3-ium) chloride

HRID 11986

Reaction equation

HRID 11986 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:11].[S:12]([CH2:21][CH2:22][NH:23][C:24](=[O:27])[CH2:25]Cl)[S:13][CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][Cl:19]>C(#N)C>[Cl-:19].[S:12]([CH2:21][CH2:22][NH:23][C:24](=[O:27])[CH2:25][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N+:2]([CH3:1])=[C:3]1[CH3:11])[S:13][CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N+:2]([CH3:1])=[C:3]1[CH3:11].[Cl-:19]

Participants

4

Reactant 2

HCID 3126931,2-DimethylbenzimidazoleHCID 20525005N,N'-(disulfanediyldiethane-2,1-diyl)bis(2-chloroacetamide)

Product 1

HCID 866335761,1'-{disulfanediylbis[ethane-2,1-diylimino(2-oxoethane-2,1-diyl)]}bis(2,3-dimethyl-1H-benzimidazol-3-ium) chlorideYield 129.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of compound 1,2-dimethyl-1H-benzimidazole (2.93 g, 20 mmol) and N,N′-(disulfanediyldiethane-2,1-diyl)bis(2-chloroacetamide) (1.53 g, 5 mmol) in 20 ml of acetonitrile was heated to reflux for 24 h. After cooling, the resulting white solids were collected by filtration and washed with ethyl acetate and dichloromethane to afford 1.94 g of a white powder. Analyses were in accordance with the expected structure.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. temperatureAfter cooling
  4. filtrationthe resulting white solids were collected by filtration
  5. washwashed with ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-ec8236a187c1419c973899f581646a85
Source dataset
uspto-grants-2010_06
Patent number
US07727287B2

Linked notes

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