Triethylamine → Cyenopyrafen

HRID 1096682Notes

Reaction equation

HRID 1096682 reaction equation
[O:1]=[C:2]([C:16]1[N:20]([CH3:21])[N:19]=[C:18]([CH3:22])[C:17]=1[CH3:23])[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=1)[C:4]#[N:5].C(N(CC)CC)C.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]>O1CCCC1>[CH3:33][C:32]([CH3:35])([CH3:34])[C:31]([O:1]/[C:2](/[C:16]1[N:20]([CH3:21])[N:19]=[C:18]([CH3:22])[C:17]=1[CH3:23])=[C:3](\[C:6]1[CH:7]=[CH:8][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:10][CH:11]=1)/[C:4]#[N:5])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 119839523-Oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)propionitrile

Product 1

HCID 18772482CyenopyrafenYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
7 °C

Procedure

In a 10 L-reaction flask, 594 g (1.92 mol) of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl) propionitrile and 6000 g of tetrahydrofuran were added, 214 g (2.11 mol) of triethyl amine was added and then 255 g (2.11 mol) of pivaloyl chloride was added dropwise at 25 to 27° C. over 1 hour. After reacting for 20 hours, tetrahydrofuran was removed by concentrating under a reduced pressure, and then 1800 g of toluene and 1800 g of water were added to separate out toluene phase. After distilling out toluene, 794 g of hexane was added and dissolved, and crystallization was carried out by gradually cooling to 7° C. After filtering, the crystal was washed with 1000 g of hexane cooled at 5° C., dried to obtain 554 g (yield 73.4%) of (2E)-3-(2,2-dimethylpropanoyloxy)-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl) acrylonitrile.

Workup

  1. additionwere added
  2. customtetrahydrofuran was removed
  3. concentrationby concentrating under a reduced pressure
  4. addition1800 g of toluene and 1800 g of water were added
  5. customto separate out toluene phase
  6. distillationAfter distilling out toluene, 794 g of hexane
  7. additionwas added
  8. dissolutiondissolved
  9. customcrystallization
  10. filtrationAfter filtering
  11. washthe crystal was washed with 1000 g of hexane
  12. temperaturecooled at 5° C.
  13. customdried

Sources & evidence

ORD record
ord-d06757a304d443b0896e3443d9b03dad
Source dataset
uspto-grants-2012_03
Patent number
US08138368B2

Reaction notes

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