Tetrahydrofuran → 1-(N,N-dibutylaminocarbonyloxy)-2-phenylphenanthroimidazole

HRID 622330Notes

Reaction equation

HRID 622330 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH:16]=[CH:17][C:18]=3[C:5]=2[N:4]=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31]([N:35]([CH2:39][CH2:40][CH2:41][CH3:42])[C:36](Cl)=[O:37])[CH2:32][CH2:33][CH3:34].O1CCCC1>C(OCC)(=O)C.O>[CH2:31]([N:35]([C:36]([O:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH:16]=[CH:17][C:18]=3[C:5]=2[N:4]=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:37])[CH2:39][CH2:40][CH2:41][CH3:42])[CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 83371Dibutylcarbamoyl chlorideHCID 867424231-Hydroxy-2-phenylphenanthroimidazole

Product 1

HCID 867424221-(N,N-dibutylaminocarbonyloxy)-2-phenylphenanthroimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

10 parts of 1-hydroxy-2-phenylphenanthroimidazole, 8 parts of anhydrous potassium carbonate and 6.7 parts of N,N-dibutylcarbamyl chloride in 100 parts of tetrahydrofuran are refluxed for 5 hours. 100 parts of water and 200 parts of ethyl acetate are then added. The organic phase is washed with water, dried over sodium sulfate and evaporated down under reduced pressure. When the residue is left to stand, 6.6 parts of a solid which has a melting point of 120° C. and is pure according to thin layer chromatography are obtained.

Workup

  1. washThe organic phase is washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated down under reduced pressure
  4. waitWhen the residue is left
  5. customare obtained

Sources & evidence

ORD record
ord-c08a6d890a5b4754bc072ba3271cb4fa
Source dataset
uspto-grants-1988_09
Patent number
US04770976

Reaction notes

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