Hydrochloric Acid → HCID 178479535, compound

HRID 1639118Notes

Reaction equation

HRID 1639118 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13](=[NH:16])[NH:14][OH:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].Cl.C([O-])(O)=O.[Na+].CO.C(Cl)(Cl)[Cl:30]>CCOCC.CO>[ClH:30].[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13](=[NH:16])[NH:14][OH:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:18])[F:19]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 21584188Chloroform methanolHCID 178513270HCID 178513270, compound

Product 1

HCID 178479535HCID 178479535, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

In a 125 ml, 3-necked round bottom flask equipped with thermometer, condenser, stir bar and heated in an oil bath was added 1.69 g (0.0067 mole) of F, 0.507 g (0.0073 mole, 1.1 equiv.) of hydroxylamine hydrochloride, 0.409 g (0.0073 mole, 1.1 equiv.) of potassium hydroxide and 40 ml of abs. ethanol. This yellow slurry was stirred and heated to reflux for 3 hours, then stirred at room temperature overnight. TLC showed the reaction to be complete, so the slurry was filtered and rinsed with 50 ml of ethanol. The ethanol was evaporated off under vacuum to yield a tan solid. This solid was dissolved in 200 ml of ethyl acetate and washed with 2×100 ml of distilled water, dried over MgSO4, filtered and evaporated to yield 1.92 g of crude product. This crude product was eluted through a silica gel column using 60% EtOAc/hexane. After collecting the fractions and TLCing them, the clean fractions were combined and evaporated to yield 1.7 g of 5-(4-hydroxy-3-trifluoromethylphenyl)-N-hydroxy-2-furancarboximidamide (E1). E1 was dissolved in 50 ml of ether in a 100 ml flask and then acidified with methanolic/HCl to a pH of 1-3. After stirring for a few minutes, a pink solid precipitated. This was filtered and air dried to yield 1.68 g. TLC showed two spots, so the crude product was dissolved in 10 ml of methanol, then the pH was adjusted to basic side with 10% NaHCO3 solution to remove the HCl salt. A white solid precipitated and was filtered and air dried to yield 1.49 g. TLC--Rf =0.45 (10% MeOH/CHCl3) gave one spot. This pure product was dissolved in 50 ml of ether and acidified with methanolic/HCl solution to a pH of 1-3 and a white solid precipitated. This white solid was filtered and air dried to yield 1.4 g of 5-(4-hydroxy-3-trifluoromethylphenyl)-N-hydroxy-2-furancarboximidamide hydrochloride (E2). TLC--Rf =0.27 (10% MeOH/CHCl3). IR and NMR were consistent with a structure of E2.

Workup

  1. customa pink solid precipitated
  2. filtrationThis was filtered
  3. customair dried
  4. customto yield 1.68 g
  5. customto remove the HCl salt
  6. customA white solid precipitated
  7. filtrationwas filtered
  8. customair dried
  9. customto yield 1.49 g
  10. customa white solid precipitated
  11. filtrationThis white solid was filtered
  12. customair dried

Sources & evidence

ORD record
ord-aa57e63d712f4d05a0e5f8f56baea8d2
Source dataset
uspto-grants-1989_11
Patent number
US04882354

Reaction notes

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