Triethylamine → HCID 12067747, compound

HRID 988916Notes

Reaction equation

HRID 988916 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[N:11]1([CH2:16][CH2:17][CH2:18][NH2:19])[CH:15]=[CH:14][N:13]=[CH:12]1.C(N(CC)CC)C>COCCOC>[N:11]1([CH2:16][CH2:17][CH2:18][NH:19][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 12067747HCID 12067747, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 28.2 g (0.2 mol) of 1-fluoro-4-nitrobenzene, 31.3 g (0.25 mol) of 3-imidazol-1-ylpropylamine and 34.8 ml of triethylamine in 30 ml of 1,2-dimethoxyethane was heated for half an hour with stirring. The mixture was poured into 1.5 liters of ice-cold water and the crystalline precipitate was filtered off, reimpasted in water and then in isopropyl alcohol and dried under vacuum at 40° C. over phosphorus pentoxide. Yellow crystals (36.6 g) which, after purification by recrystallization from refluxing 96° ethanol, melted at 124° C., were obtained, the elemental analysis of which, calculated for C12H14N4O2, was:

Workup

  1. temperaturewas heated for half an hour
  2. filtrationthe crystalline precipitate was filtered off
  3. dry with materialin isopropyl alcohol and dried under vacuum at 40° C. over phosphorus pentoxide
  4. customYellow crystals (36.6 g) which, after purification
  5. customby recrystallization
  6. temperaturefrom refluxing 96° ethanol, melted at 124° C.
  7. customwere obtained

Sources & evidence

ORD record
ord-5d6259ef0d87419c930c96b27e97ce99
Source dataset
uspto-grants-2003_10
Patent number
US06638321B1

Reaction notes

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