1,1'-Carbonyldiimidazole → HCID 23294394, compound

HRID 1955187Notes

Reaction equation

HRID 1955187 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][Br:9])=[CH:4][C:3]=1[N+:12]([O-])=O.C1N=CN([C:20](N2C=NC=C2)=[O:21])C=1>C1COCC1.[Pd]>[O:21]=[C:20]1[N:1]=[C:2]2[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][Br:9])=[CH:4][C:3]2=[N:12]1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 154854442-(4-Amino-3-nitrophenoxy)ethyl bromide

Product 1

HCID 23294394HCID 23294394, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-amino-3-nitrophenoxy)ethyl bromide (980 mg, 7.59 mmol) in dry THF (20 mL) was shaken over 5% Pd/C (80 mg) under H2 (20-30 psi) for 5 h, then filtered. To the filtrate was added CDI (2.4 g, 14.8 mmol). The mixture was stirred at room temperature under N2 for 4 h, then refluxed for 14 h. The mixture was evaporated, then the residual solid was washed with CHCl3 (3×15 mL), and dried to give 407 mg (21%) of the title compound as an off-white powder, mp 225-6° C. 1H NMR (DMSO-d6): 3.747 (t, 2H, J=5.5), 4.234 (t, 2H, J=5.5), 6.52-6.54 (m, 2H), 6.792 (d, 1H, J=9), 10.399 (s, 1H), 10.521 (s, 1H).

Workup

  1. filtrationfiltered
  2. temperaturerefluxed for 14 h
  3. customThe mixture was evaporated
  4. washthe residual solid was washed with CHCl3 (3×15 mL)
  5. customdried

Sources & evidence

ORD record
ord-193746efc1704730a88c7079d7303764
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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