Ethanol → HCID 123493647, compound

HRID 1893605Notes

Reaction equation

HRID 1893605 reaction equation
C(O)C.[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH3:43])=[C:10]([N:12]([CH2:29][C:30]([N:32]([N:34]2[CH2:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:35]2)[CH3:33])=[O:31])[CH2:13][C:14]([NH:16][CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH3:21])=[O:15])[CH:11]=1)#[N:5].C([O-])(=O)C.[Na+].[Cl-].[OH:50][NH3+:51]>C(OCC)(=O)C.CCCCCC>[NH2:5][C:4](=[N:51][OH:50])[C:6]1[CH:7]=[CH:8][C:9]([CH3:43])=[C:10]([N:12]([CH2:29][C:30]([N:32]([N:34]2[CH2:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:42]2)[CH3:33])=[O:31])[CH2:13][C:14]([NH:16][CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:20][CH3:21])=[O:15])[CH:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 123702801HCID 123702801, compound

Product 1

HCID 123493647HCID 123493647, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To ethanol (20 ml) were added the compound (1.10 g, 2.00 mmol) of Example 2, step A, sodium acetate (347 mg, 4.23 mmol) and hydroxylammonium chloride (292 mg, 4.20 mmol) and the mixture was heated under reflux for 210 min. The reaction mixture was cooled, diluted with an ethyl acetate-hexane=1:1 mixed solvent, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give a colorless amorphous solid (1.19 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 210 min
  3. temperatureThe reaction mixture was cooled
  4. washwashed with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8f3e0141406941bd95c8f14451bd8bb1
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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