Imidazole → HCID 86747812, compound

HRID 1033035Notes

Reaction equation

HRID 1033035 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[CH:13][C:6]([NH:7][C:8](=[O:12])[CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.N1C=CN=C1.[H-].[Na+].[C:24](Cl)(=[O:28])/[CH:25]=[CH:26]/[CH3:27]>O1CCCC1>[C:10](/[C:9](=[C:24](\[OH:28])/[CH:25]=[CH:26][CH3:27])/[C:8]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:15])([F:16])[F:1])=[CH:14][CH:13]=1)=[O:12])#[N:11]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 643131trans-Crotonyl chlorideHCID 38238032-Cyano-N-[4-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 86747812HCID 86747812, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0 6.0 g (0.026 mole) of 4'-trifluoromethyl-cyanoacetanilide in 200 ml of dry tetrahydrofuran were stirred under nitrogen during the addition of 0.02 g of imidazole and 1.95 g (0.065 mole) of sodium hydride 80% oil dispersion. The suspension was stirred for 2 hours at room temperature and then was cooled to -78° C. before the dropwise addition of 3.06 ml (0.031 mole) of freshly distilled crotonyl chloride. The mixture was stirred at -78° C. for 2 hours, poured onto a mixture of dilute hydrochloric acid/ice and filtered. The solid was dissolved in dichloromethane, washed with water, dried over magnesium sulfate and the solvent was removed under reduced pressure to obtain 7.65 g (99%) of colorless crystals of the expected compound.

Workup

  1. stirringThe mixture was stirred at -78° C. for 2 hours
  2. filtrationfiltered
  3. dissolutionThe solid was dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5097fcbdf75544319ad43d21b2096d3b
Source dataset
uspto-grants-1994_05
Patent number
US05308865

Reaction notes

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