Triphenylphosphine → HCID 21890160, compound

HRID 721627Notes

Reaction equation

HRID 721627 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.CO[C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][C:34]=1OC)[N:31]=[CH:30][CH:29]=[C:28]2OC1C=CC(NC(NC2CCNCC2)=O)=CC=1.[C:54]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:55]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N:31]1([CH2:30][CH2:29][CH2:28][O:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)=[CH:17][CH:18]=2)[C:32]2[C:27](=[CH:26][CH:25]=[CH:34][CH:33]=2)[CH:55]=[CH:54]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 17755504HCID 17755504, compoundHCID 21890637HCID 21890637, compound

Product 1

HCID 21890160HCID 21890160, compoundYield 4.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenol (100 mg), the compound (1) (59 mg), and triphenylphosphine (106 mg) were dissolved in tetrahydrofuran (3 ml) to prepare a solution. Diethyl azodicarboxylate (0.063 ml) was then added to the solution, and the mixture was stirred at room temperature for 3 hr. The solvent was removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate, followed by washing with saturated brine. The extract was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography using hexane/acetone for development. Diethyl ether was added to the purification product, and the precipitated crystal was collected by filtration and was washed to give the title compound (3 mg, yield 2%). Mass spectrometry value (FD-MS, m/z): 455 (M+)

Workup

  1. customto prepare a solution
  2. customThe solvent was removed by distillation under the reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washby washing with saturated brine
  6. dry with materialThe extract was then dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customThe residue was purified by thin-layer chromatography
  9. additionDiethyl ether was added to the purification product
  10. filtrationthe precipitated crystal was collected by filtration
  11. washwas washed

Sources & evidence

ORD record
ord-957d0a302b304efd9642c576da1427c3
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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