Sodium hydride → HCID 14052582, compound

HRID 330089Notes

Reaction equation

HRID 330089 reaction equation
[H-].[Na+].F[C:4]1[C:21]([CH3:22])=[C:20]([F:23])[C:19]([F:24])=[CH:18][C:5]=1[C:6]([C:8](=[CH:14][NH:15][CH2:16][CH3:17])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7]>O1CCOCC1>[CH2:16]([N:15]1[C:4]2[C:5](=[CH:18][C:19]([F:24])=[C:20]([F:23])[C:21]=2[CH3:22])[C:6](=[O:7])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14]1)[CH3:17]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178464351HCID 178464351, compound

Product 1

HCID 14052582HCID 14052582, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the cooled mixture of 55% sodium hydride (0.47 g) in anhydrous dioxane (20 ml) was added ethyl 2-(2,4,5-trifluoro-3-methylbenzoyl)-3-ethylaminoacrylate (2.6 g) during 10 minutes with stirring. After stirring for 40 minutes at room temperature, the reacting mixture was poured into ice-water (50 ml), the resulting precipitate was collected by filtration, washed with chilled water and ether successively and recrystallized from dichloromethane-n-hexane to give the title compound (1.6 g) as colorless prisms, mp 177°-179.5° C.

Workup

  1. stirringAfter stirring for 40 minutes at room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with chilled water and ether successively
  4. customrecrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-d59df91b6bf7474caf2cc0723e20e67e
Source dataset
uspto-grants-1990_01
Patent number
US04894458

Reaction notes

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