Hydroxyamine hydrochloride → HCID 85417866, compound

HRID 553335Notes

Reaction equation

HRID 553335 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-c78df7d1d5484863996bbb6f3f6d8280
Source dataset
uspto-grants-2011_11
Patent number
USRE042890E1

Reaction notes

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