Triethylamine → HCID 58542581, compound

HRID 1843067Notes

Reaction equation

HRID 1843067 reaction equation
[Cl:1][C:2]1[C:3]([NH:8][NH2:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[F:17][C:18]([F:34])([F:33])[C:19]([C:29](F)(F)[F:30])=[C:20](F)[C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23]>C(#N)C>[Cl:1][C:2]1[C:3]([N:8]2[C:29]([F:30])=[C:19]([C:18]([F:34])([F:33])[F:17])[C:20]([C:21]([F:26])([F:27])[C:22]([F:23])([F:24])[F:25])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74105Perfluoro(2-methyl-2-pentene)HCID 5561003-Chloro-2-hydrazinylpyridine

Product 1

HCID 58542581HCID 58542581, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.0 g (7.0 mmol) of 3-chloro-2-hydrazinopyridine is suspended in 2.9 ml (21 mmol) of triethylamine and 40.0 ml of acetonitrile and, at −65° C., added to 2.1 g (7 mmol) of (1,1,1,3,4,4,5,5,5-nonafluoro-2-(trifluoromethyl)pent-2-ene. The reaction mixture is slowly heated to room temperature and then stirred at room temperature for 60 hours. The solid is filtered off and afterwashed with diethyl ether. The solvent is removed under reduced pressure on a rotary evaporator. The product is extracted from the residue three times with cyclohexane. The organic phases are combined and the solvent is removed under reduced pressure on a rotary evaporator. This gives 1.95 g of 3-chloro-2-[5-fluoro-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-1-yl]pyridine (73%) as an orange oil.

Workup

  1. filtrationThe solid is filtered off
  2. customThe solvent is removed under reduced pressure on a rotary evaporator
  3. extractionThe product is extracted from the residue three times with cyclohexane
  4. customthe solvent is removed under reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-097dd41f051f4a95afbbf2bd13ffce5c
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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