Triethylamine → HCID 54258996, compound

HRID 1357428Notes

Reaction equation

HRID 1357428 reaction equation
[CH3:1][N:2]1[C:6]([Cl:7])=[C:5]([C:8]([OH:21])=[C:9]([C:12]2[S:13][CH:14]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[N:16]=2)[C:10]#[N:11])[C:4]([C:22]([F:25])([F:24])[F:23])=[N:3]1.C(N(CC)CC)C.[C:33](Cl)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>C1COCC1>[CH3:1][N:2]1[C:6]([Cl:7])=[C:5]([C:8]([O:21][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[C:9]([C:12]2[S:13][CH:14]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[N:16]=2)[C:10]#[N:11])[C:4]([C:22]([F:25])([F:23])[F:24])=[N:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 136067619HCID 136067619, compound

Product 1

HCID 54258996HCID 54258996, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 g of 3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-2-(4-tert-butylthiazol-2-yl)-3-hydroxyacrylonitrile and 0.14 g of triethylamine were added to 15 ml of THF at room temperature and stirred to give a uniform solution. 0.16 g of pivaloyl chloride was dropwise added to the solution with cooling with ice, then gradually heated, and stirred at room temperature for 8 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed thrice with saturated saline. After having been dried over sodium sulfate, the resulting product was passed through a short column filled with silica gel. The solvent was distilled off under reduced pressure, and the residual product was applied to silica gel thin-layer chromatography (developer solvent: chloroform) to obtain 0.16 g of 3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-2-(4-tert-butylthiazol-2-yl)-3-pivaloyloxyacrylonitrile (III-6) and 0.35 g of its geometric isomer (III-15).

Workup

  1. customto give a uniform solution
  2. temperaturewith cooling with ice
  3. temperaturegradually heated
  4. stirringstirred at room temperature for 8 hours
  5. extractionextracted with ethyl acetate
  6. washwashed thrice with saturated saline
  7. dry with materialAfter having been dried over sodium sulfate
  8. additionfilled with silica gel
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d1697a3ae8514cfbbc72196083125f1f
Source dataset
uspto-grants-2003_07
Patent number
USRE038188E1

Reaction notes

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