Potassium Carbonate → N'-Hydroxythiophene-2-carboximidamide

HRID 462170Notes

Reaction equation

HRID 462170 reaction equation
[C:1]([C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)#[N:2].Cl.[NH2:9][OH:10].C([O-])([O-])=O.[K+].[K+]>C(O)C.O>[S:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[C:1](=[N:9][OH:10])[NH2:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 660872-ThiophenecarbonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 2760620N'-Hydroxythiophene-2-carboximidamideYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 21.8 g (0.20 mole) of 2-cyanothiophene in 500 ml of ethanol, 13.9 g (0.20 mole) of hydroxylamine HCl is added, followed by the addition of 13.8 g (0.10 mole) of K2CO3 in 50 ml of water. The mixture is refluxed for 16 hours, cooled and diluted with 200 ml of water. After removing the ethanol in vacuo, the product precipitates out of the aqueous residue. It is collected by filtration, washed with water and dried to yield 22.4 g (80%) of product, m.p. 70°-75°.

Workup

  1. temperatureThe mixture is refluxed for 16 hours
  2. temperaturecooled
  3. customAfter removing the ethanol in vacuo
  4. customthe product precipitates out of the aqueous residue
  5. filtrationIt is collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-9e3de2bcf77e4844acc9acdb34837ae2
Source dataset
uspto-grants-1977_12
Patent number
US04065563

Reaction notes

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