Sodium hydride → HCID 86662106, compound

HRID 2067127Notes

Reaction equation

HRID 2067127 reaction equation
F[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=[O:16])/[C:8](=[N:14]/[NH2:15])/[C:9]([O:11][CH2:12][CH3:13])=[O:10].[I:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1.[H-].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[I:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][N:15]2[C:2]3[CH:6]=[CH:5][S:4][C:3]=3[C:7](=[O:16])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:14]2)=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 24758Sodium hydride2×HCID 516892Sodium Bicarbonate2×HCID 9542584-Iodobenzyl bromideHCID 178472859HCID 178472859, compound

Product 1

HCID 86662106HCID 86662106, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl(2Z)-3-(3-fluoro-2-thienyl)-2-hydrazono-3-oxopropanoate (5.73 g, 23.5 mmol) and 4-iodobenzylbromide (7.31 g, 24.6 mmol, 1.05 equiv) were dissolved in degassed N,N-dimethylformamide (47 mL) and cooled to 0° C. Sodium hydride (1.03 g, 25.8 mmol, 1.1 equiv, 60% dispersion in mineral oil) was added portionwise over 30 minutes and was stirred for an additional 2 hours at 0° C. Additional sodium hydride (1.03 g, 25.8 mmol, 1.1 equiv, 60% dispersion in mineral oil) was added and the mixture was stirred at 0° C. for an additional 1 hour. The mixture was carefully treated with sodium bicarbonate (5 mL, aqueous saturated) and then poured into sodium bicarbonate (200 mL, aqueous saturated) and water (250 mL). The aqueous layer was treated with ethyl acetate (400 mL), upon which a thick precipitate formed. The mixture was filtered and the solid was collected and dried in vacuo, providing the titled compound. The filtrate (organic and aqueous) was extracted with ethyl acetate (2×400 mL) and the combined organic extracts were washed with brine (50 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 1:100; hexanes:ethyl acetate), providing additional titled compound.

Workup

  1. stirringthe mixture was stirred at 0° C. for an additional 1 hour
  2. customformed
  3. filtrationThe mixture was filtered
  4. customthe solid was collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e172d3be7d2b48b5a9be38e507772f27
Source dataset
uspto-grants-2012_10
Patent number
US08293744B2

Reaction notes

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