Potassium thiocyanate → (2,2-Dichloro-3,3-dimethylcyclopropyl)methyl thiocyanate

HRID 1981332Notes

Reaction equation

HRID 1981332 reaction equation
[Cl:1][C:2]1([Cl:9])[C:4]([CH3:6])([CH3:5])[CH:3]1[CH2:7]Cl.[S-:10][C:11]#[N:12].[K+]>C(O)C>[Cl:1][C:2]1([Cl:9])[C:4]([CH3:6])([CH3:5])[CH:3]1[CH2:7][S:10][C:11]#[N:12]

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 277527310229-40-0

Product 1

HCID 13313519(2,2-Dichloro-3,3-dimethylcyclopropyl)methyl thiocyanateYield 85.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.87 g of 2,2-dichloro-3,3-dimethyl-1-chloromethylcyclopropane and 1.0 g of potassium thiocyanate were suspended in 20 ml of ethanol, and the suspension was refluxed for 12 hours. Ethanol was evaporated, and 20 ml of water was added. The mixture was extracted with toluene. The toluene layer was washed with water and dried over sodium sulfate. The toluene was then evaporated under reduced pressure to give 1.80 g of 2,2-dichloro-3,3-dimethylcyclopropylmethyl thiocyanate, the desired compound shown above. The boiling point of the product was 115° C. at 200 mmHg.

Workup

  1. temperaturethe suspension was refluxed for 12 hours
  2. customEthanol was evaporated
  3. addition20 ml of water was added
  4. extractionThe mixture was extracted with toluene
  5. washThe toluene layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customThe toluene was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-b3a5eab249d44e83841cdbc99e247a0d
Source dataset
uspto-grants-1985_04
Patent number
US04514418

Reaction notes

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