Hydrochloric Acid → HCID 178527958, compound

HRID 1979633Notes

Reaction equation

HRID 1979633 reaction equation
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([NH:18][NH2:19])(=O)[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.[OH-].[Na+].Cl>C(O)C.O>[C:1]1([N:7]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[N:18][N:19]=[C:8]2[SH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3767IsoniazidHCID 7673Phenyl IsothiocyanateHCID 14798Sodium Hydroxide

Product 1

HCID 178527958HCID 178527958, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A one liter round bottomed flask, fitted with a reflux condenser, nitrogen inlet and magnetic stirrer bar, is charged with 40.5 g (0.30 mol) of phenyl isothiocyanate and 41.845 g (0.30 mol) of isonicotinic acid hydrazide in 300 ml of absolute ethanol. The mixture is heated to reflux for 3 hours. The resulting solid is filtered and washed with ethanol and then added to an aqueous solution of sodium hydroxide (prepared by dissolving 16.8 g, 0.42 mol, of sodium hydroxide in 240 ml of water). The mixture is heated to reflux for 5 hours and then stirred at ambient temperature for 18 hours. The solution is treated with 100 ml of distilled water to dissolve the gel which has formed. The solution is made acidic (to pH 2) with concentrated HCl and cooled with ice. The solid is filtered, taken up in 600 ml of warm absolute ethanol and filtered again to afford approximately 70 g (92%) of slightly wet titled product with a melting point of 288°-290° C. IR (nujol shows a peak at 1900 cm-1 ; UV (95% ethanol) shows peaks at 257 nm and 317 nm; NMR (DMSO-d6 δ) 8.5 and 7.2-7.6; the mass spectra shows a strong molecular ion peak at m/e 254, with fragment ions at 253, 195 and 149.

Workup

  1. customA one liter round bottomed flask, fitted with a reflux condenser, nitrogen inlet and magnetic stirrer bar
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 3 hours
  4. filtrationThe resulting solid is filtered
  5. washwashed with ethanol
  6. temperatureThe mixture is heated
  7. temperatureto reflux for 5 hours
  8. dissolutionto dissolve the gel which
  9. customhas formed
  10. temperaturecooled with ice
  11. filtrationThe solid is filtered
  12. filtrationfiltered again

Sources & evidence

ORD record
ord-aa7e73e819134ffe9d2c7af2f1d4fa65
Source dataset
uspto-grants-1984_11
Patent number
US04481360

Reaction notes

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