Dichloromethane → 1,3-Diamino-2-(4-methoxyphenyl)imidazolium chloride

HRID 1194424Notes

Reaction equation

HRID 1194424 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)(O[NH2:24])=O)C=CC=CC=1.[Cl:31]CCl>>[Cl-:31].[NH2:1][N+:2]1[CH:6]=[CH:5][N:4]([NH2:24])[C:3]=1[C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 221673981-Amino-2-(p-methoxyphenyl)imidazole

Product 1

HCID 703609421,3-Diamino-2-(4-methoxyphenyl)imidazolium chloride

Procedure

0.1 g of 1-amino-2-(4-methoxyphenyl)imidazole is dissolved in 10 ml of dichloromethane. The solution is treated portionwise during 8 days with 0.29 g of O-diphenylphosphinylhydroxylamine, evaporated and the residue is suspended in 10 ml of water. The difficultly soluble diphenylphosphinic acid is removed by filtration and the filtrate is placed on a column loaded with Amberlite IRA 400 (chloride), whereupon the column is eluted with water. There is obtained 1,3-diamino-2-(4-methoxyphenyl)imidazolium chloride.

Workup

  1. customevaporated
  2. customThe difficultly soluble diphenylphosphinic acid is removed by filtration
  3. washis eluted with water

Sources & evidence

ORD record
ord-75439abee5ba4a92a810ceec45b5a418
Source dataset
uspto-grants-1989_03
Patent number
US04814332

Reaction notes

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