Hydrochloric Acid → HCID 12888761, compound

HRID 1153848Notes

Reaction equation

HRID 1153848 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][N:4]([CH3:9])[N:3]=1.F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>C1(C)C=CC=CC=1.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[CH3:9][N:4]1[CH:5]=[C:6]([C:7]#[N:8])[C:2]([NH:1][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])=[N:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 738951-Fluoro-2-nitrobenzeneHCID 106542131-Methyl-3-amino-4-cyanopyrazole

Product 1

HCID 12888761HCID 12888761, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

3-Amino-1-methylpyrazole-4-carbonitrile (Helv. Chim. Acta (1959) 42, 763) (7.5 g) and 2-fluoronitrobenzene (8.4 g) were stirred in toluene (120 ml) with Adogen 464 (3.0 g) and potassium carbonate (16.5 g) at 60° C. 50% Sodium hydroxide solution (0.1 ml) was added and the mixture was heated under reflux for 2 hours. The mixture was poured on to dilute hydrochloric acid, extracted, the aqueous layer washed with toluene and the combined extracts washed twice with water. After evaporation the residue was crystallised from ethanol (750 ml) to give the title compound, m.p. 172° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted
  4. washthe aqueous layer washed with toluene
  5. washthe combined extracts washed twice with water
  6. customAfter evaporation the residue
  7. customwas crystallised from ethanol (750 ml)

Sources & evidence

ORD record
ord-3358a32e5f894ba1ad957872b767d9eb
Source dataset
uspto-grants-1984_12
Patent number
US04486591

Reaction notes

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