Hydroxyamine hydrochloride → HCID 85417866, compound

HRID 131998Notes

Reaction equation

HRID 131998 reaction equation
[Br:1][C:2]1[CH:25]=[CH:24][C:5]([C:6](=O)[CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[C:17]2[C:18]([NH2:22])=[N:19][O:20][N:21]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Cl.[NH2:32][OH:33]>C(O)C>[Br:1][C:2]1[CH:25]=[CH:24][C:5]([C:6](=[N:32][OH:33])[CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[C:17]2[C:18]([NH2:22])=[N:19][O:20][N:21]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 11383949HCID 11383949, compound

Product 1

HCID 85417866HCID 85417866, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[1-(4-bromophenacyl)-1H-benzimidazol-2-yl]-furazan-3-ylamine (0.083 g, 0.21 mmol, prepared according to Example 1), sodium bicarbonate (0.021 g, 0.25 mmol) and hydroxylamine hydrochloride (0.014 g, 0.21 mmol) in ethanol (5 ml) is refluxed for 20 hours. Partitioning of the reaction mixture between ethyl acetate and water, separation of the organic phase followed by drying and evaporation of the solvent gives the crude product. Purification by chromatography on silicagel yields the title compound as an E/Z-mixture, m.p. 198-201° C.

Workup

  1. temperatureis refluxed for 20 hours
  2. customPartitioning of the reaction mixture between ethyl acetate and water, separation of the organic phase
  3. customby drying
  4. customevaporation of the solvent
  5. customgives the crude product
  6. customPurification by chromatography on silicagel

Sources & evidence

ORD record
ord-fb5162e2dbda41d3b43e92eb53d22fa5
Source dataset
uspto-grants-2008_06
Patent number
US07385061B2

Reaction notes

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