Hydroxyamine hydrochloride → HCID 85607801, compound

HRID 330284Notes

Reaction equation

HRID 330284 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][C:14]([CH2:16][C:17]#[N:18])=[CH:13][C:12]=2[CH:19]=1>CO>[OH:3][N:2]=[C:17]([NH2:18])[CH2:16][C:14]1[S:15][C:11]2[CH:10]=[CH:9][C:8]([Br:7])=[CH:19][C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 1481935323799-63-5

Product 1

HCID 85607801HCID 85607801, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of hydroxylamine hydrochloride (3.86 g, 0.056 mol) in MeOH (100 mL) was added sodium methoxide (25 wt % in MeOH, 10.33 g, 0.056 mol). Stirring was continued for 15 minutes and 5-bromo-2-benzthiophenylacetonitrile (7.0 g, 0.028 mol) was added. The resulting mixture was refluxed for 2 days, cooled, and concentrated. The residue was diluted with H2O. The solid was collected by filtration, purified by column chromatography (eluant: EtOAc/hexane, 2:3) to give 4.0 g (50%) of product as a white solid.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 days
  2. temperaturecooled
  3. concentrationconcentrated
  4. additionThe residue was diluted with H2O
  5. filtrationThe solid was collected by filtration
  6. custompurified by column chromatography (eluant: EtOAc/hexane, 2:3)

Sources & evidence

ORD record
ord-553c7208aaeb4f83922e0b49e46ec1f1
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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