Sodium Cyanide → Cypermethrin

HRID 2059329Notes

Reaction equation

HRID 2059329 reaction equation
[C-]#N.[Na+].[N:4]12[CH2:11]CN(CC1)CC2.[O:12]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl:27][C:28]([Cl:38])=[CH:29][CH:30]1[CH:32]([C:33](Cl)=[O:34])[C:31]1([CH3:37])[CH3:36].C(=O)([O-])[O-].[Na+].[Na+]>O.CCCCCCCC>[Cl:27][C:28]([Cl:38])=[CH:29][CH:30]1[CH:32]([C:33]([O:23][CH:22]([C:11]#[N:4])[C:21]2[CH:24]=[CH:25][CH:26]=[C:19]([O:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:20]=2)=[O:34])[C:31]1([CH3:36])[CH3:37]

Participants

8

Reactant 5

HCID 8929Sodium CyanideHCID 9237DabcoHCID 10340Sodium CarbonateHCID 382843-PhenoxybenzaldehydeHCID 94551Permethric chloride

Product 1

HCID 2912Cypermethrin

Reagents, catalysts & solvents 2

HCID 356OctaneSolventHCID 962WaterSolvent

Procedure

Under a dry nitrogen atmosphere a mixture of sodium cyanide (5.9 g, 0.12 mole) and 1,4-diazabicyclo[2.2.2]octane (0.22 g, 0.002 mole) in 10 grams of water was stirred at room temperature. During a one hour period a solution of 3-phenoxybenzaldehyde (20.6 g, 0.1 mole) and 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (24.1 g, 0.105 mole) in 120 ml of n-octane was added to the reaction mixture. After complete addition, the reaction mixture was stirred for one hour. An aqueous solution containing 20% sodium carbonate was added to the reaction mixture and the total warmed to 60°. The organic phase was separated and washed with water, dried over anhydrous magnesium sulfate and filtered. The solvent was removed from the filtrate under reduced pressure to yield α-cyano-3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. additionAfter complete addition
  2. stirringthe reaction mixture was stirred for one hour
  3. additionwas added to the reaction mixture
  4. temperaturethe total warmed to 60°
  5. customThe organic phase was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-7a73abd81d924b6581874ce13907ca8b
Source dataset
uspto-grants-1982_03
Patent number
US04322534

Reaction notes

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