Nitroxyl → HCID 178510834, compound

HRID 1684636Notes

Reaction equation

HRID 1684636 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]4[NH:26]C(=O)[O:24][N:23]=4)=[CH:17][CH:16]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NO.Cl.N=O>CO>[OH:24][NH:23][C:22](=[NH:26])[CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][C:10]2[N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][CH:9]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 945NitroxylHCID 443297Hydroxyamine hydrochlorideHCID 136118794HCID 136118794, compound

Product 1

HCID 178510834HCID 178510834, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

Preparation of: 3-[(4-(2-(2-Phenyl-4-oxazolyl)ethoxy)phenyl)methyl]1,2,4-oxadiazolin-5-one. ##STR28## Part A Preparation of: ##STR29## To a cooled (0° C.) solution of 0.88 g of Na in 80 mL of anhydrous MeOH was added 2.67 g of NH2OH HCl followed by a solution of the iminoether of Example 12 Part C Method 2 in 100 mL of anhydrous MeOH. The reaction mixture was allowed to warm to 25° C. and was stirred for 18 hours. The residue, after removal of solvent, was partitioned between 200 mL of H2O and 700 mL of EtOAc. The solid was removed by filtration and washed with H2O and EtOAc. The combined organic phases were washed with H2O and combined with the solid. After removal of the solvent, the residue was recrystallized from MeOH. The filtrate was diluted with Et2O and the resulting solid was filtered to give 4.14 g of crude N-hydroxy-4-[2-(2-phenyl-4-oxazolyl)ethoxy]benzeneethanimidamide. FD-MS: m/e 337.

Workup

  1. custom##STR28## Part A Preparation of: ##STR29## To
  2. customThe residue, after removal of solvent
  3. customwas partitioned between 200 mL of H2O and 700 mL of EtOAc
  4. customThe solid was removed by filtration
  5. washwashed with H2O and EtOAc
  6. washThe combined organic phases were washed with H2O
  7. customAfter removal of the solvent
  8. customthe residue was recrystallized from MeOH
  9. additionThe filtrate was diluted with Et2O
  10. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-288ac11e97824ce49923baa4c59e5b6c
Source dataset
uspto-grants-1997_06
Patent number
US05641796

Reaction notes

Loading…