Phenol → HCID 434301, compound

HRID 1199475Notes

Reaction equation

HRID 1199475 reaction equation
[CH3:1][N:2]1[C:6]([N+]([O-])=O)=[C:5]([N+:10]([O-:12])=[O:11])[N:4]=[CH:3]1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>O>[CH3:1][N:2]1[C:6]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([N+:10]([O-:12])=[O:11])[N:4]=[CH:3]1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 294841-Methyl-4,5-dinitroimidazole

Product 1

HCID 434301HCID 434301, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 17.2 g (0.1 mole) of 1-methyl-4,5-dinitroimidazole, 11.2 g (0.12 mole) of phenol and 4.4 g (0.11 mole) of NaOH in 200 ml of water was stirred for 1 hour at 50° C. Thereafter, the solution was diluted with a further 300 ml of water and was cooled. The precipitated crystals were filtered off under suction and recrystallized from water. 21.0 g (96%) of 1-methyl-4-nitro-5-phenoxyimidazole of melting point 116°-118° C. were obtained.

Workup

  1. temperaturewas cooled
  2. filtrationThe precipitated crystals were filtered off under suction
  3. customrecrystallized from water

Sources & evidence

ORD record
ord-112f95165b23468485a6f13edfc2b191
Source dataset
uspto-grants-1990_02
Patent number
US04900825

Reaction notes

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