Water → 2-(2,6-Dichloro-4-trifluoromethylphenylhydrazino)succinonitrile

HRID 1937100Notes

Reaction equation

HRID 1937100 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][N:14]=[C:15]([CH2:18][C:19]#[N:20])[C:16]#[N:17].[C-]#N.[Na+].O.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][NH:14][CH:15]([CH2:18][C:19]#[N:20])[C:16]#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 853091952-(2,6-Dichloro-4-trifluoromethylphenylhydrazono)succinonitrile

Product 1

HCID 539339412-(2,6-Dichloro-4-trifluoromethylphenylhydrazino)succinonitrileYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(2, 6-Dichloro-4-trifluoromethylphenylhydrazono)succinonitrile (0.296 g, 1 mmol), sodium cyanide (0.196 g, 4 equivalents), water (1 ml) and acetic acid (5 ml) were added successively to a sealed tube. After reacting for 40 hours at 20° C. the mixture was added to saturated sodium bicarbonate solution, extracted (dichloromethane), washed (water), dried (magnesium sulphate) and evaporated to give a mixture which contained 40% of the desired title compound, NMR 3.1 (m,2H), 4.5(m,1H), 5.89(m, 1H), 6.94(d,1H), 7.71(s,2H), together with 60% of unchanged starting hydrazone.

Workup

  1. extractionextracted (dichloromethane)
  2. washwashed (water)
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated
  5. customto give a mixture which

Sources & evidence

ORD record
ord-f13b7357037442f78f1f873cee598513
Source dataset
uspto-grants-2002_05
Patent number
US06392081B1

Reaction notes

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