Hydroxyamine hydrochloride → HCID 73769874, compound

HRID 263086Notes

Reaction equation

HRID 263086 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[K+].[Cl:9][C:10]1[CH:26]=[CH:25][C:13]([O:14][C:15]2[CH:24]=[CH:23][C:18]([O:19][CH2:20][C:21]#[N:22])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1>O.C(O)CCC>[ClH:9].[Cl:9][C:10]1[CH:26]=[CH:25][C:13]([O:14][C:15]2[CH:24]=[CH:23][C:18]([O:19][CH2:20][C:21](=[N:2][OH:3])[NH2:22])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516893Potassium BicarbonateHCID 23350111HCID 23350111, compound

Product 1

HCID 73769874HCID 73769874, compoundYield 157.8%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolvent2×HCID 962WaterSolvent2×

Procedure

A suspension of 5.37 g (0.0772 mol) of hydroxylamine hydrochloride and of 7.72 g (0.0772 mol) of potassium bicarbonate in 8 ml of water is added, all at once, to a suspension of 10 g (0.0385 mol) of 4-(4-chlorophenoxy)-phenoxy-acetonitrile prepared as indicated in Example 29a), in 24 ml of n-butanol. The mixture is heated to the reflux temperature for 1 hour, the butanol is driven off, the residue is taken up in water and the insoluble matter is extracted with diethyl ether. The organic phase is washed with water, dried over dry sodium sulphate and evaporated, and the residue obtained is purified by washing with hot diisopropyl ether to give 10 g of brilliant white needles.

Workup

  1. customprepared
  2. temperatureThe mixture is heated to the reflux temperature for 1 hour
  3. extractionthe insoluble matter is extracted with diethyl ether
  4. washThe organic phase is washed with water
  5. dry with materialdried over dry sodium sulphate
  6. customevaporated
  7. customthe residue obtained
  8. customis purified
  9. washby washing with hot diisopropyl ether

Sources & evidence

ORD record
ord-35f680461bd5445bb087ab9549636418
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

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