Potassium Hydroxide → HCID 54295410, compound

HRID 268091Notes

Reaction equation

HRID 268091 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]#[N:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Cl.[NH2:17][OH:18].[OH-].[K+]>C(O)C>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14](=[N:17][OH:18])[NH2:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 21553319HCID 21553319, compound

Product 1

HCID 54295410HCID 54295410, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 13 g (0.060 mole) of 5-(p-methylthiophenyl)-2-furonitrile, 4.5 g (0.065 mole) of hydroxylamine hydrochloride, 4.2 g (0.065 mole) of KOH, and 160 ml of absolute ethanol was refluxed for 11/2 hours and then kept overnight at room temperature. The insoluble material was removed by filtration and discarded. The filtrate was added to ice/water and the resulting solid was dissolved in refluxing ethyl acetate, Darcoed, and filtered. The filtrate was heated to reflux and hexane was added to the cloud point. This mixture was cooled in an ice bath with the resulting solid being filtered and air dried to yield 10 g (67%). An analytical sample was prepared by drying a sample in the vacuum pistol at the temperature of refluxing CHCl3, m.p. 148°-150°.

Workup

  1. temperaturewas refluxed for 11/2 hours
  2. customThe insoluble material was removed by filtration
  3. additionThe filtrate was added to ice/water
  4. dissolutionthe resulting solid was dissolved
  5. temperaturein refluxing ethyl acetate, Darcoed
  6. filtrationfiltered
  7. temperatureThe filtrate was heated
  8. temperatureto reflux
  9. additionhexane was added to the cloud point
  10. temperatureThis mixture was cooled in an ice bath with the resulting solid being
  11. filtrationfiltered
  12. customair dried
  13. customto yield 10 g (67%)
  14. customAn analytical sample was prepared
  15. dry with materialby drying a sample in the vacuum pistol at the temperature of refluxing CHCl3, m.p. 148°-150°

Sources & evidence

ORD record
ord-88fd160de9074d5290a77e4df8abb7c5
Source dataset
uspto-grants-1976_03
Patent number
US03946049

Reaction notes

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