Sodium hydride → HCID 13342085, compound

HRID 543549Notes

Reaction equation

HRID 543549 reaction equation
[N+:1]([C:4]1[C:5]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[C:15]([OH:17])=O)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[H-].[Na+].[O:20]1[CH:22]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:26]=2[CH3:32])[CH2:21]1>CN(C=O)C>[CH3:32][C:26]1[C:27]([CH3:31])=[CH:28][CH:29]=[CH:30][C:25]=1[O:24][CH2:23][CH:22]([OH:20])[CH2:21][N:1]1[C:4]2[CH:9]=[CH:8][CH:7]=[N:6][C:5]=2[N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[C:15]1=[O:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27661831-(3-Nitropyridin-2-yl)prolineHCID 126196772-[(2,3-Dimethylphenoxy)methyl]oxirane

Product 1

HCID 13342085HCID 13342085, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the product of Example 1 (2.7 g., 0.015 mole) in 40 ml. of dry DMF was added 0.6 g. of sodium hydride (0.025 mole of 50% dispersion in mineral oil). After the evolution of gases subsided, 2.6 g. (0.015 mole) of 1,2-epoxy-3-[2,3-dimethylphenoxy]propane was added. The reaction mixture was stirred overnight and DMF was evaporated in vacuo and the residue was extracted with 200 ml. of diethyl ether. The ether layer was dried and concentrated in vacuo to 30 ml. TLC indicated the presence of two products, one of which is a major component (about 80%). The ether layer was cooled overnight and the separated solid was filtered and recrystallized from diethyl ether to afford 1.8 g. (51% yield) of the title compound m.p. 123°-125° C.

Workup

  1. customDMF was evaporated in vacuo
  2. extractionthe residue was extracted with 200 ml
  3. dry with materialThe ether layer was dried
  4. concentrationconcentrated in vacuo to 30 ml
  5. temperatureThe ether layer was cooled overnight
  6. filtrationthe separated solid was filtered
  7. customrecrystallized from diethyl ether
  8. customto afford 1.8 g

Sources & evidence

ORD record
ord-d671c811263940d790142addf0ba7d66
Source dataset
uspto-grants-1984_05
Patent number
US04446323

Reaction notes

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