Hydroxyamine hydrochloride → Ethyl 2-oximinooxamate

HRID 1834214Notes

Reaction equation

HRID 1834214 reaction equation
[Na].Cl.[NH2:3][OH:4].[CH3:5][CH2:6][O:7][C:8]([C:10]([NH2:12])=S)=[O:9]>C(O)C>[CH3:5][CH2:6][O:7][C:8](/[C:10](/[NH2:12])=[N:3]/[OH:4])=[O:9]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 2733398Ethyl thiooxamateHCID 5360545Sodium

Product 1

HCID 9614369Ethyl 2-oximinooxamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 8.98 gm. (0.39 mole) of sodium in 180 ml. of anhydrous ethanol is added to a solution of 26.8 gm. (0.386 mole) of hydroxylamine hydrochloride in 270 ml. of hot ethanol. The precipitate is removed by filtration. To the stirred filtrate is added 34.2 gm. (0.26 mole) of ethyl 2-thiooxamate. The yellow solution is allowed to stand overnight. The solution is evaporated to dryness in vacuo and the residue recrystallized from diethyl ether. There is obtained 21.2 g. (68%) of a yellow solid melting at 99°-101° C.

Workup

  1. customThe precipitate is removed by filtration
  2. additionTo the stirred filtrate is added 34.2 gm
  3. customThe solution is evaporated to dryness in vacuo
  4. customthe residue recrystallized from diethyl ether
  5. customThere is obtained 21.2 g

Sources & evidence

ORD record
ord-27ce73cae8864ea6955dd2fa4a9941f8
Source dataset
uspto-grants-1978_01
Patent number
US04069332

Reaction notes

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