Triethylamine → HCID 86760552, compound

HRID 917363Notes

Reaction equation

HRID 917363 reaction equation
[F:1][C:2]([F:10])=[C:3]([CH3:9])[CH2:4][CH2:5][CH2:6][CH2:7][SH:8].[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][N:13]=1.C(N(CC)CC)C>O1CCCC1.O>[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([S:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([CH3:9])=[C:2]([F:10])[F:1])=[O:17])=[CH:14][N:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27821656-Chloronicotinoyl ChlorideHCID 23020242HCID 23020242, compound

Product 1

HCID 86760552HCID 86760552, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture consisting of 1.00 g (6.3 mmol) of 6-chloronicotinic acid, 5 ml of thionyl chloride and three drops of N,N-dimethylformamide was stirred under heating and refluxing for 3 hours. After the reaction, excess thionyl chloride was removed under reduced pressure, followed by the addition of 10 ml of toluene and removing the solvent again under reduced pressure to obtain crystal of 6-chloronicotinoyl chloride. In a separate vessel, 0.50 g (3.0 mmol) of 6,6-difluoro-5-methyl-5-hexene-1-thiol and 0.80 g (4.5 mmol) of 6-chloronicotinoyl chloride were dissolved in 10 ml of tetrahydrofuran, followed by the drop-wise addition of 0.50 g (4.9 mmol) of triethylamine at room temperature and stirring at the same temperature for 1 hour. The reaction liquid was then poured in water and extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (diisopropyl ether:hexane=1:6) to obtain 0.80 g (yield: 87%) of S-(6,6-difluoro-5-methyl-5-hexenyl) 6-chlorothionicotinate.

Workup

  1. customThe reaction liquid
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (diisopropyl ether:hexane=1:6)

Sources & evidence

ORD record
ord-9a3734aaa72045cdb9455dbedb453d25
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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