Water → HCID 10975969, compound

HRID 1762385Notes

Reaction equation

HRID 1762385 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1.C1(P(C2C=CC=CC=2)(O[NH2:24])=O)C=CC=CC=1.O>O1CCCC1.CN1CCCC1=O>[NH2:24][N:5]1[CH:6]=[C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:8]=[C:4]1[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 178432485HCID 178432485, compound

Product 1

HCID 10975969HCID 10975969, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

7.92 g (171 mmol) of sodium hydride (55-60 percent dispersion in oil) are washed with absolute tetrahydrofuran. A solution of 13.2 g (83 mmol) of 2-methyl-4-phenylimidazole in 356 ml of N-methylpyrrolidone is added dropwise at 0°. The mixture is subsequently stirred at room temperature until the evolution of gas is no longer observed. 39.6 g (171 mmol) of O-diphenylphosphinylhydroxylamine are added portionwise thereto and the mixture is stirred for a further 18 hours. 400 ml of water are added thereto. The mixture is stirred for 1 hour and extracted four times with 1300 ml of methylene chloride each time. The extract is dried over sodium sulphate and evaporated. The residue is place on a column loaded with 700 g of silica gel (particle size 0.063-0.200 mm) amnd the product is eluted with methylene chloride/ethanol (98:2). The oil (N-amino-2-methyl-4-phenylimidazole) obtained after concentration is dissolved with 1150 ml of methylene chloride and treated with 13.94 g (60 mmol) of O-diphenylphosphinylhydroxylamine. After stirring for 3 days a further 13.94 g (60 mmol) of O-diphenylphosphinylhydroxylamine are added thereto and the mixture is stirred for a further 24 hours. The mixture is concentrated and the residue is placed on a column loaded with Amberlite IRA 400 (chloride). Elution is carried out with water. The aqueous solution is evaporated and the residue is placed on a column loaded with 300 g of silica gel (particle size 0.063-0.200 mm). The product is eluted with methylene chloride/ethanol (1:9). From the eluate there is obtained 1,3-diamino-2-methyl-4-phenylimidazolium chloride of melting point 162°-163°.

Workup

  1. stirringthe mixture is stirred for a further 18 hours
  2. stirringThe mixture is stirred for 1 hour
  3. extractionextracted four times with 1300 ml of methylene chloride each time
  4. dry with materialThe extract is dried over sodium sulphate
  5. customevaporated
  6. washis eluted with methylene chloride/ethanol (98:2)

Sources & evidence

ORD record
ord-4d3db8b0b2564f8687ad2e56f27216b1
Source dataset
uspto-grants-1989_05
Patent number
US04831151

Reaction notes

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