Ammonia → 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonitrile

HRID 2057513Notes

Reaction equation

HRID 2057513 reaction equation
Cl[CH:2]([CH2:12][C:13]([Cl:16])([Cl:15])Cl)[C:3]([CH3:11])([CH3:10])[CH:4]([C:8]#[N:9])C(O)=O.N>CN(C)C=O.O>[Cl:16][C:13]([Cl:15])=[CH:12][CH:2]1[C:3]([CH3:10])([CH3:11])[CH:4]1[C:8]#[N:9]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 204348434,6,6,6-Tetrachloro-2-cyano-3,3-dimethylhexanoic acid

Product 1

HCID 128981733-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonitrileYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

4-Chloro-2-cyano-3,3-dimethyl-6,6,6-trichlorohexanoic acid (40 g) was dissolved in dimethyl formamide (66 ml) and the solution, at room temperature, was saturated with gaseous ammonia with no external cooling. The solution was stirred at 140° C. for 5 hours, then diluted with water and extracted with ether (3×100 ml). The ether solution was washed with saturated NaCl, dried over MgSO4 and evaporated to afford Compound A as a yellow oil (purity 85%) which partly crystallized on standing. Yield 79%.

Workup

  1. customat room temperature
  2. extractionextracted with ether (3×100 ml)
  3. washThe ether solution was washed with saturated NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-bd1e5a5e77bf49c7bc7ba1c55741634c
Source dataset
uspto-grants-1980_07
Patent number
US04211720

Reaction notes

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