1,1'-Carbonyldiimidazole → HCID 136118794, compound

HRID 1684637Notes

Reaction equation

HRID 1684637 reaction equation
[OH:1][NH:2][C:3](=[NH:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][C:14]2[N:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:17][CH:18]=2)=[CH:7][CH:6]=1.[C:26](N1C=CN=C1)(N1C=CN=C1)=[O:27]>C1COCC1>[C:19]1([C:16]2[O:17][CH:18]=[C:14]([CH2:13][CH2:12][O:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][C:3]4[NH:25][C:26](=[O:27])[O:1][N:2]=4)=[CH:10][CH:9]=3)[N:15]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178510834HCID 178510834, compound

Product 1

HCID 136118794HCID 136118794, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4.06 g of the amidoxime from Example 14 Part A, 150 mL of THF and 1.98 g of carbonyldiimidazole was heated at reflux for 7 hours, cooled to 25° C., and stirred another 16 hours. The solvent was removed in vacuo. The residue was dissolved in 600 mL of EtOAc, washed with H2O and dried over anhydrous Na2SO4. The residue, obtained after filtration and evaporation of the solvent, was recrystallized from EtOH to give 3.11 g of 3-[(4-(2-(2-phenyl-4-oxazolyl)ethoxy)phenyl)-methyl]1,2,4-oxadiazolin-5-one, (71% mp 154.5°-157.5° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in 600 mL of EtOAc
  5. washwashed with H2O
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe residue, obtained
  8. filtrationafter filtration and evaporation of the solvent
  9. customwas recrystallized from EtOH

Sources & evidence

ORD record
ord-24e6addac12949caa16824cde00caf11
Source dataset
uspto-grants-1997_06
Patent number
US05641796

Reaction notes

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