Triphenylphosphine → HCID 22288647, compound

HRID 968308Notes

Reaction equation

HRID 968308 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[CH:9][C:10]([OH:19])=[N:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[N:20]1([CH2:25][C:26]2[CH:35]=[CH:34][C:29]([O:30][CH2:31][CH2:32]O)=[CH:28][CH:27]=2)[CH:24]=[CH:23][N:22]=[CH:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:20]1([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:30][CH2:31][CH2:32][O:19][C:10]3[N:11]=[C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=4)[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:8][CH:9]=3)=[CH:34][CH:35]=2)[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15594572HCID 15594572, compoundHCID 178516755HCID 178516755, compound

Product 1

HCID 22288647HCID 22288647, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5,6-Di(2-pyridyl)-2-pyrazinol (1.21 g), 2-[4-(1H-imidazolylmethyl)phenoxy]-1-ethanol (1.05 g), and triphenylphosphine (1.27 g) were dispersed in tetrahydrofuran (30 mL). A 40% solution (2.10 g) of diethyl azodicarboxylate in toluene was added dropwise to the dispersion under ice cooling, and the resultant mixture was allowed to react overnight, while the temperature of the mixture was gradually elevated to room temperature. After completion of reaction, ethyl acetate was added to the reaction mixture, and the ethyl acetate layer was washed with water. The washed product was dried over sodium sulfate anhydrate, and the residual solvent was removed through distillation under reduced pressure. The thus-yielded residue was purified by means of a silica gel column and recrystallized from ethyl acetate, to thereby yield 960 mg of Compound (1B) of the present invention as pale yellow crystals (yield 44.0%).

Workup

  1. customto react overnight, while the temperature of the mixture
  2. customwas gradually elevated to room temperature
  3. additionwas added to the reaction mixture
  4. washthe ethyl acetate layer was washed with water
  5. dry with materialThe washed product was dried over sodium sulfate anhydrate
  6. customthe residual solvent was removed through distillation under reduced pressure
  7. customThe thus-yielded residue was purified by means of a silica gel column
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c817d518f95b4810a0e6e8f96bdb3b47
Source dataset
uspto-grants-2005_10
Patent number
US06958353B2

Reaction notes

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