Sodium hydride → HCID 70254767, compound

HRID 1938836Notes

Reaction equation

HRID 1938836 reaction equation
[F:1][C:2]([F:18])([F:17])[S:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:16])[CH2:13][C:14]#[N:15])=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1.Cl.O>C1COCC1.N1C=CN=C1>[F:18][C:2]([F:17])([F:1])[S:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:16])[C:13]([C:14]#[N:15])=[C:24]([CH:21]2[CH2:23][CH2:22]2)[OH:25])=[CH:9][CH:10]=1)=[O:4]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 77637Cyclopropanecarbonyl chlorideHCID 10802374HCID 10802374, compoundHCID 21885828Hydrate;hydrochloride

Product 1

HCID 70254767HCID 70254767, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 795ImidazoleCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.1 g (0.0112 mole) of N-(4'-trifluoromethylsulfinyl-phenyl)-cyanoacetamide in 100 ml of anhydrous THF and 10 mg of catalytic imidazole and 0.75 g (0.0246 mole) of sodium hydride (80% oil dispersion) were stirred at room temperature for 90 minutes and then 1.32 ml (0.0146 mole) of cyclopropylcarbonyl chloride were added dropwise. The solution was stirred at room temperature for 10 minutes, was poured into a 1M HCl/water mixture and was filtered. The product was dissolved in dichloromethane and chromatographed on a short silica column (dichloromethane) to obtain 2.54 g (66% yield) of N-(4'-trifluoromethylsulfinyl-phenyl)-2-cyano-3-cyclopropyl-3-hydroxy-prop-2-enamide melting at 155°-157° C.

Workup

  1. filtrationwas filtered
  2. dissolutionThe product was dissolved in dichloromethane
  3. customchromatographed on a short silica column (dichloromethane)

Sources & evidence

ORD record
ord-a0c668a5d441459fb5c37b4ef43fd915
Source dataset
uspto-grants-1997_12
Patent number
US05693844

Reaction notes

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