Sodium Chloride → 1-Amino-2-(p-methoxyphenyl)imidazole

HRID 1194429Notes

Reaction equation

HRID 1194429 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)=[CH:7][CH:6]=1.[H][H].C1(P(C2C=CC=CC=2)(O[NH2:27])=O)C=CC=CC=1.[Cl-].[Na+]>O1CCCC1>[NH2:27][N:15]1[CH:14]=[CH:13][N:12]=[C:11]1[C:8]1[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 124631352-(4-Methoxyphenyl)-1H-imidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 221673981-Amino-2-(p-methoxyphenyl)imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9.0 g of sodium hydride (55 percent dispersion in oil) are suspended in 600 ml of absolute tetrahydrofuran. 8.5 g of 2-(p-methoxyphenyl)imidazole are added thereto within 5 minutes. The mixture is stirred until hydrogen is no longer liberated (1 hour). Then, 34.5 g of O-diphenylphosphinylhydroxylamine are added portionwise thereto at 10° and the mixture is stirred at 10° for an additional 40 minutes and then at room temperature for 18 hours. Saturated sodium chloride solution is added thereto at 5° and the mixture is subsequently extracted with methylene chloride/methanol (99.5:0.5). The extract is dried over sodium sulfate and evaporated. There is obtained 1-amino-2-(p-methoxyphenyl)imidazole as a brown oil.

Workup

  1. custom(1 hour)
  2. waitat room temperature for 18 hours
  3. extractionat 5° and the mixture is subsequently extracted with methylene chloride/methanol (99.5:0.5)
  4. dry with materialThe extract is dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-885ae286270444e1994e74bf2a1adccd
Source dataset
uspto-grants-1989_03
Patent number
US04814332

Reaction notes

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