Hydroxyamine hydrochloride → Ethyl 2-oximinooxamate

HRID 236987

Reaction equation

HRID 236987 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-2038fc3009464cafb1a1921d9b62ec37
Source dataset
uspto-grants-1979_06
Patent number
US04159336

Linked notes

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