Ethylenediamine → HCID 178422332, compound

HRID 1019082Notes

Reaction equation

HRID 1019082 reaction equation
[CH3:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([CH3:11])[C:3]=1[N:12]=C=S.[CH2:15]([NH2:18])[CH2:16][NH2:17].[CH2:19](Cl)Cl>CO>[CH3:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([CH3:11])[C:3]=1[NH:12][N:17]1[CH2:16][CH2:15][N:18]=[CH:19]1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6344Dichloromethane2×HCID 178422331HCID 178422331, compound

Product 1

HCID 178422332HCID 178422332, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4,6-dimethyl-5-isothiocyanatobenzimidazole (250 mg, 1.23 mmol) in methylene chloride (5 mL) is added dropwise to a solution of ethylenediamine (370 mg, 6.2 mmol) in methylene chloride (5 mL). The resulting solution is stirred at room temperature for 15 minutes then rotary evaporated. The residue is dissolved in methanol (10 mL) and to this solution is added mercuric acetate (390 mg, 1.23 mmol). The resulting reaction mixture is stirred at room temperature for 1 hour, filtered through a pad of silica gel and rotary evaporated. The residue is purified by chromatography on silica gel (70:30:0.5 methylene chloride:methanol:ammonium hydroxide) to afford 4,6-dimethyl-5-(2-imidazolinylamino)benzimidazole as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. stirringis stirred at room temperature for 1 hour
  3. filtrationfiltered through a pad of silica gel and rotary evaporated
  4. customThe residue is purified by chromatography on silica gel (70:30:0.5 methylene chloride:methanol:ammonium hydroxide)

Sources & evidence

ORD record
ord-9a18f313d1a74287addddade140c7fb6
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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