Sodium Hydroxide → HCID 14951553, compound

HRID 1974789Notes

Reaction equation

HRID 1974789 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[N:8]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[CH:11][C:10]=2[Cl:17])[N:7]=[C:6]([C:18]#[N:19])[C:5]=1[S:20]C#N>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.C(Cl)(Cl)Cl>[NH2:3][C:4]1[N:8]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[CH:11][C:10]=2[Cl:17])[N:7]=[C:6]([C:18]#[N:19])[C:5]=1[S:20][S:20][C:5]1[C:6]([C:18]#[N:19])=[N:7][N:8]([C:9]2[C:10]([Cl:17])=[CH:11][C:12]([Cl:16])=[CH:13][C:14]=2[Cl:15])[C:4]=1[NH2:3]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 19101957HCID 19101957, compound

Product 1

HCID 14951553HCID 14951553, compoundYield 93.5%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Benzyltriethylammonium chloride (0.32 g, 0.0014 mole) and a solution of NaOH (6.0 g, 0.15 mol) in water (20 cc) were added with stirring to a suspension of 5-amino-3-cyano-4-thiocyanato-1-(2,4,6-trichlorophenyl) -1H-pyrazole (16.2 g, 0.047 mol) in CHCl3 (180 cc). The resulting mixture was stirred under laboratory atmosphere, at ambient temperature, for 3.1 hours, at the end of which time a TLC of a reaction aliquot portion showed that the reaction was complete. The yellow-coloured solid product was separated off by filtration, was washed with water, and was then dissolved in ethyl acetate, the solution being subjected to an extraction with water (2×200 ml) and to a dehydration over MgSO4. A dehydration in a vacuum oven at a temperature of 70° to 75° C. for approximately 16 hours gave 4,4'-dithiobis[5-amino-3-cyano-1-(2,4,6-trichlorophenyl) -1H-pyrazole] (14.0 g, 93.5%) in the form of a yellow-coloured solid substance.

Workup

  1. customThe yellow-coloured solid product was separated off by filtration
  2. washwas washed with water
  3. dissolutionwas then dissolved in ethyl acetate
  4. extractionthe solution being subjected to an extraction with water (2×200 ml) and to a dehydration over MgSO4

Sources & evidence

ORD record
ord-a463730d2e804a0eb4940c53cb98c5e7
Source dataset
uspto-grants-1994_02
Patent number
US05283337

Reaction notes

Loading…