1-Methylimidazole → HCID 86614743, compound

HRID 2108286Notes

Reaction equation

HRID 2108286 reaction equation
[Br:1][CH2:2][CH2:3][N:4]([CH2:22][CH3:23])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N:12][C:13]2[S:14][C:15]([N+:19]([O-:21])=[O:20])=[C:16]([Cl:18])[N:17]=2)=[CH:7][CH:6]=1.[CH3:24][N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1>C(#N)C>[Br-:1].[Cl:18][C:16]1[N:17]=[C:13]([N:12]=[N:11][C:8]2[CH:9]=[CH:10][C:5]([N:4]([CH2:22][CH3:23])[CH2:3][CH2:2][N:27]3[CH:28]=[CH:29][N+:25]([CH3:24])=[CH:26]3)=[CH:6][CH:7]=2)[S:14][C:15]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 86614745HCID 86614745, compound

Product 1

HCID 86614743HCID 86614743, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.20 g N-(2-bromoethyl)-4-[(4-chloro-5-nitro-1,3-thiazol-2-yl)diazenyl]-N-ethylaniline is dissolved in 20 ml acetonitrile followed by subsequent addition of 5.99 g 1-methyl-1H-imidazole. The reaction mixture is stirred under reflux for 3 days and allowed to cool to room temperature. The resulted precipitate is filtered off, washed with acetonitrile, and dried in vacuum at 40° C. 0.43 g 1-{2-[{4-[(4-chloro-5-nitro-1,3-thiazol-2-yl)diazenyl]phenyl}(ethyl)amino]ethyl}-3-methyl-1H-imidazol-3-ium bromide is obtained as a bordeaux red powder.

Workup

  1. temperatureunder reflux for 3 days
  2. filtrationThe resulted precipitate is filtered off
  3. washwashed with acetonitrile
  4. customdried in vacuum at 40° C

Sources & evidence

ORD record
ord-d2028ffdbcee470fae6ff01221f2372d
Source dataset
uspto-grants-2009_04
Patent number
US07513916B2

Reaction notes

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