Ethanol → HCID 178421796, compound

HRID 1900795Notes

Reaction equation

HRID 1900795 reaction equation
[C:1]([CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=O)[CH2:9][CH2:8]3)#[N:2].Cl.[NH2:19][OH:20].C(N(CC)CC)C.C([OH:30])C>>[CH3:15][C:13]1[CH:14]=[C:5]2[CH2:4][CH:3]([C:1]([NH2:2])=[O:30])[O:17][C:6]2=[C:7]2[C:12]=1[NH:11][C:10](=[N:19][OH:20])[CH2:9][CH2:8]2

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 23369829HCID 23369829, compound

Product 1

HCID 178421796HCID 178421796, compound

Conditions

Temperature
90 °C

Procedure

The compound obtained in Example 262 (0.63 g, 2.76 mmol) was dissolved in ethanol (50 ml), to which hydroxylamine hydrochloride (0.38 g, 5.5 mmol) and triethylamine (1.15 ml, 8.3 mmol) were added. The mixture was refluxed with heat at 90° C. for 1 hour. The solvent was distilled off under reduced pressure. To the residue, water and chloroform were added. The precipitate was collected by filtration, and washed with water and chloroform. Subsequently, the washed material was dissolved in hot methanol and chloroform, followed by drying over magnesium sulfate. When the solvent was distilled off under reduced pressure, 0.47 g of the title compound was obtained as a white solid (65%). This solid was recrystallized from methanol--ether to obtain colorless crystals (mp.: 251°-254° C.).

Workup

  1. additionwere added
  2. temperatureThe mixture was refluxed
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue, water and chloroform were added
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water and chloroform
  7. dissolutionSubsequently, the washed material was dissolved in hot methanol
  8. dry with materialby drying over magnesium sulfate
  9. distillationWhen the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ad72443fe5024b1e842fb40bbd5ea0c5
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

Loading…