Water → HCID 40126890, compound

HRID 601719Notes

Reaction equation

HRID 601719 reaction equation
[CH2:1](N)[CH2:2]CC.[C:6]([N:13]1[CH:17]=[CH:16]N=[CH:14]1)([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)=[O:7].O>C1COCC1>[CH2:17]([N:13]([CH3:14])[C:6]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)=[O:7])[CH2:16][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8007ButylamineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 40126890HCID 40126890, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butylamine (20 g, 0.23 mol) was dissolved in 100 mL of THF and added at a quick dropwise rate to a suspension of carbonyldiimidazole (37.2 g, 0.23 mol) in 200 mL of THF. The solution was headed to reflux for 3 h, then cooled, treated with 200 mL of water, and partitioned into ethyl acetate. The organic layer was separated and then washed with brine, dried with MgSO4, and then concentrated to the crude imidazolide, which was purified by distillation at 108° C. and 600 mtorr to provide a pure oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.86 (s, 1H), 7.21 (s, 1H), 7.10 (s, 1H), 3.40 (t, J=7.60 Hz, 2H), 3.06 (s, 3H), 1.61 (m, 2H), 1.31 (m, 2H), 0.93 (t, J=7.23 Hz, 3H).

Workup

  1. temperatureto reflux for 3 h
  2. temperaturecooled
  3. custompartitioned into ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated to the crude imidazolide, which
  8. distillationwas purified by distillation at 108° C.
  9. custom600 mtorr to provide a pure oil

Sources & evidence

ORD record
ord-4b58b45e34f047b08b678837bb83d96a
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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