Nitrite → 3,4-Bistrifluoromethylbenzonitrile

HRID 847540

Reaction equation

HRID 847540 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])N.S(=O)(=O)(O)O.N([O-])=O.[Na+].N([O-])=O.[C-]#N.[Na+].[Cu][C:32]#[N:33].C(=O)([O-])O.[Na+]>O.S([O-])([O-])(=O)=O.[Ni+2]>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[C:32]#[N:33]

Participants

10

Reactant 7

HCID 946NitriteHCID 1118Sulfuric AcidHCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 15485793,4-Bis(trifluoromethyl)anilineHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 147932713,4-BistrifluoromethylbenzonitrileYield 63%

Reagents, catalysts & solvents 2

HCID 24586Nickel SulfateCatalystHCID 962WaterSolvent4×

Conditions

Temperature
100 °C

Procedure

229 g (1 mole) of 3,4-bistrifluoromethyl-aniline were diazotized in a solution of 350 g of concentrated sulphuric acid in 1.25 1 of water using 70 g of sodium nitrite in 140 ml of water. After the diazonium salt solution had become nitrite-free, it was added dropwise to a solution of 550 ml of water, 210 g of sodium cyanide, 10 g of copper (I) cyanide, 500 g of sodium hydrogen carbonate and 9 g of nickel sulphate ×7 H2O heated to 100° C. The product was isolated from the reaction mixture by steam distillation and subsequently distilled again. 152 g of product having a boiling point at 14 mbar of 85° C. and a melting point of 71° to 72° C. were obtained. This corresponds to a yield of 63% of theory.

Workup

  1. customThe product was isolated from the reaction mixture by steam distillation
  2. distillationsubsequently distilled again
  3. customat 14 mbar of 85° C.
  4. customa melting point of 71° to 72° C. were obtained

Sources & evidence

ORD record
ord-0c4b417b96ef4ab5af5fca5c67cd6ce8
Source dataset
uspto-grants-1992_08
Patent number
US05142092

Linked notes

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