Sodium Carbonate → 2-(4-bromophenyl)-N'-hydroxyethanimidamide

HRID 1057498Notes

Reaction equation

HRID 1057498 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.CO.[OH2:13].Cl.O[NH2:16].C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:16])=[N:10][OH:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 27914Benzeneacetonitrile, 4-bromo-HCID 443297Hydroxyamine hydrochlorideHCID 22242641Methanol--water (1/1)

Product 1

HCID 27571142-(4-bromophenyl)-N'-hydroxyethanimidamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring solution of 2-(4-bromophenyl) ethanenitrile in methanol/water (1 eq/1 eq, 0.1 M) was added hydroxyamine hydrochloride (2.1 eq) and sodium carbonate (2.0 eq). The reaction was stirred at 60° C. for 5 hrs. The reaction was diluted with ethyl acetate and separated. The organic layer was washed with 10% hydochloric acid and separated. The aqueous layer was neutrized with 10% sodium carbonate and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated in vacuo to afford the product. EI-MS m/z 229, 231(M+H)+

Workup

  1. customseparated
  2. washThe organic layer was washed with 10% hydochloric acid
  3. customseparated
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford the product

Sources & evidence

ORD record
ord-a30f35d5b3c8445999d45cec90e9a443
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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