Hydrochloric Acid → Fenamol

HRID 2379463Notes

Reaction equation

HRID 2379463 reaction equation
I.[C:2]1([N:8]=[C:9]([NH:11][NH2:12])[NH2:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:13]([O-])(O)=O.Cl.N([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.[N+]([O-])([O-])=O.[Ag+]>[C:2]1([N:8]2[C:9]([NH2:10])=[N:11][N:12]=[N:13]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 13451341HCID 13451341, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21640Fenamol

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent3×

Conditions

Temperature
50 °C

Procedure

To a warm (50° C.), stirred solution of N'-phenylhydrazinecarboximidamide monohydroiodide (86.4 g, 0.31 mol) in water (300 mL) was added in one portion 70% nitric acid (2.80 mL, 0.0435 mol) followed by dropwise addition of a solution of silver nitrate (52.66 g, 0.3100 mol) in water (70 mL). The resulting suspension was allowed to cool over 30 minutes. To the still warm (+35° C.) mixture was added concentrated hydrochloric acid (3.6 mL). The solids were filtered off and washed with hot water (60 mL). The filtrate and washings were combined and acidified with concentrated hydrochloric acid (22.3 mL). The mixture was chilled (+5° C.) and stirred while a solution of sodium nitrite (21.46 g, 0.3110 mol) in water (70 mL) was added dropwise. The temperature of the solution was kept below 8° C. by controlling the addition rate. The solution was stirred for 15 minutes. To the mixture was added powdered sodium carbonate (36.14 g, 0.341 mol) in small portions to avoid excessive foaming. The resulting precipitate was stirred for 2 days. The solids were filtered off, washed with water (3×20 mL), and dried under house vacuum/air bleed at 45° C.; yield 38.77 g (77.4%), mp=158.5°-159.5° C.

Workup

  1. temperatureto cool over 30 minutes
  2. temperatureTo the still warm (+35° C.) mixture
  3. filtrationThe solids were filtered off
  4. washwashed with hot water (60 mL)
  5. temperatureThe mixture was chilled (+5° C.)
  6. additionwas added dropwise
  7. customwas kept below 8° C.
  8. stirringThe resulting precipitate was stirred for 2 days
  9. filtrationThe solids were filtered off
  10. washwashed with water (3×20 mL)
  11. customdried under house vacuum/air
  12. custombleed at 45° C.

Sources & evidence

ORD record
ord-c9a3ecca2959414eb24516456ef5b718
Source dataset
uspto-grants-1994_11
Patent number
US05362744

Reaction notes

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