4-Nitrobenzoyl chloride → HCID 3573319, compound

HRID 1071355Notes

Reaction equation

HRID 1071355 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1)([O-:12])=[O:11]>C(O)C>[N:5]1([CH2:4][CH2:3][CH2:2][NH:1][C:17]([C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:21][CH:20]=2)=[O:18])[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 3573319HCID 3573319, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(3-aminopropyl)imidazole (3.87 ml, 33 mmol) in ethanol (65 ml) was added to 4-nitrobenzoyl chloride (4.0 g, 22 mmol) and the mixture stirred at ambient temperature for 24 hours. The volatiles were removed by evaporation and the residue was dissolved in ethyl acetate, washed with water and dried. The solvent was removed by evaporation, the residue was triturated with hexane and the product collected by filtration to give the title compound (3.2 g, 55%). NMR: 1.98 (t, 2H), 3.24 (q, 2H), 4.01 (t, 2H), 6.87 (s, 1H), 7.19 (s, 1H), 7.64 (s, 2H), 8.15 (d, 2H), 8.30 (d, 2H); 8.80 (t, 1H); m/z 275 (MH)+.

Workup

  1. customThe volatiles were removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customdried
  5. customThe solvent was removed by evaporation
  6. customthe residue was triturated with hexane
  7. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-fd61f5ce19e34ef98d9d81ee325a9744
Source dataset
uspto-grants-2005_06
Patent number
US06906065B2

Reaction notes

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