Hydroxyamine hydrochloride → HCID 86592308, compound

HRID 1835578Notes

Reaction equation

HRID 1835578 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:18]3[CH:25]=[CH:26][C:27]([C:29]#[N:30])=[CH:28][C:17]=3[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:32][OH:33].C(=O)([O-])O.[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:18]3[CH:25]=[CH:26][C:27]([C:29](=[N:32][OH:33])[NH2:30])=[CH:28][C:17]=3[N:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 10157406HCID 10157406, compound

Product 1

HCID 86592308HCID 86592308, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-(4-Benzyloxyphenyl)-5-cyano-1-cyclopentylbenzimidazole (400 mg) obtained in Example 14 was suspended in ethyl alcohol (3 ml) and water (1.5 ml), and hydroxylamine hydrochloride (141 mg) and sodium hydrogencarbonate (170 mg) were added. The mixture was refluxed under heating overnight. The reaction mixtures was allowed to cool and the precipitated crystals were collected by filtration to give the title compound (312 mg, yield 71%).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating overnight
  3. customThe reaction mixtures
  4. temperatureto cool
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-42b61df6eb7644ec94903715ca3b8120
Source dataset
uspto-grants-2004_08
Patent number
US06770666B2

Reaction notes

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