Tetrahydrofuran → HCID 22929816, compound

HRID 1295988Notes

Reaction equation

HRID 1295988 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C:24]1[C:25]([C:31]#[N:32])=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=1)=[N+]=[N-].O1CCCC1>O>[CH3:30][C:27]1[N:26]=[C:25]2[C:31]([NH2:32])=[N:20][CH2:23][C:24]2=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 229298063-(Azidomethyl)-6-methyl-2-pyridinecarbonitrile

Product 1

HCID 22929816HCID 22929816, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triphenylphosphine (11 g, 42 mmol) was added to a mixed solution of 3-(azidomethyl)-6-methyl-2-pyridinecarbonitrile (5.79 g, 33.4 mmol) in a tetrahydrofuran (120 ml) —H2O (6 ml) mixed solvent while cooling on ice and the mixture was stirred at room temperature for 22 hours. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography. The solvent was distilled off from the ethyl acetate-methanol-29% aqueous ammonia (40:10:1) elution fraction, and washing was performed with ether-n-hexane to yield the title compound (1.65 g, 34%) as a brown solid. The solvent was also distilled off from the washed mother liquor to yield the title compound (0.49 g). The NMR data for both compounds matched exactly.

Workup

  1. additionmixed solvent
  2. temperaturewhile cooling on ice
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography
  5. distillationThe solvent was distilled off from the ethyl acetate-methanol-29% aqueous ammonia (40:10:1) elution fraction
  6. washwashing

Sources & evidence

ORD record
ord-f92757abb08246bba41aea0ec66c9395
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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