Hydroxyamine hydrochloride → HCID 178479537, compound

HRID 614882Notes

Reaction equation

HRID 614882 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[NH:15][C:16]#[N:17]>CO>[ClH:7].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[NH:15][C:16]([NH:2][OH:3])=[NH:17]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 12448337HCID 12448337, compound

Product 1

HCID 178479537HCID 178479537, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 34.7 g (0.5 mol) of hydroxylamine hydrochloride in methanol and a solution of 27 g (0.5 mol) of sodium methylate in methanol is mixed whilst cooling by means of an ice bath. The NaCl is filtered off and the filtered solution is introduced into a 2,000 ml Erlenmeyer flask with magnetic stirring and cooling by means of an ice bath. A solution of 39.6 g (0.21 mol) of 2,6-dichlorophenyl-cyanamide in CH3OH is run into the preceding solution and the mixture is stirred at ambient temperature (15°-25° C.) overnight. A small amount of insoluble matter is filtered off. To the methanol solution is added twice its volume of distilled water. An insoluble material is filtered off and discarded. The filtrate is placed in a freezer for 3 hours and an insoluble material is filtered off and discarded. The filtrate is evaporated to dryness. The residue is taken up in 1,000 ml of water and the medium is rendered acid with concentrated HCl. An insoluble material is filtered off and discarded. The liquid phase is washed with ether and the pH is brought to 8 with NaOH, taking care not to exceed this value. The mixture is extracted with ether. The ether is dried over MgSO4 and the hydrochloride of the product is precipitated from the ether by bubbling-in HCl gas.

Workup

  1. temperaturewhilst cooling by means of an ice bath
  2. filtrationThe NaCl is filtered off
  3. additionthe filtered solution is introduced into a 2,000 ml Erlenmeyer flask
  4. temperaturecooling by means of an ice bath
  5. stirringthe mixture is stirred at ambient temperature (15°-25° C.) overnight
  6. filtrationA small amount of insoluble matter is filtered off
  7. additionTo the methanol solution is added twice its volume of distilled water
  8. filtrationAn insoluble material is filtered off
  9. filtrationan insoluble material is filtered off
  10. customThe filtrate is evaporated to dryness
  11. filtrationAn insoluble material is filtered off
  12. washThe liquid phase is washed with ether
  13. extractionThe mixture is extracted with ether
  14. dry with materialThe ether is dried over MgSO4
  15. customthe hydrochloride of the product is precipitated from the ether by bubbling-in HCl gas

Sources & evidence

ORD record
ord-792d94c7483946669f2d70d92374540a
Source dataset
uspto-grants-1979_03
Patent number
US04146647

Reaction notes

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