Sodium Azide → HCID 57470875, compound

HRID 2265717Notes

Reaction equation

HRID 2265717 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:11]([F:27])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C)C=O>[N:28]([C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:11]([F:27])[CH:10]=2)[N:5]=[CH:4][N:3]=1)=[N+:29]=[N-:30]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57470873Phenylmethyl N-[4-[(6-chloro-4-pyrimidinyl)oxy]-2,5-difluorophenyl]carbamate

Product 1

HCID 57470875HCID 57470875, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Benzyl [4-(4-chloropyrimidin-6-yloxy)-2,5-difluorophenyl]carbamate (1.96 g) was dissolved in N,N-dimethylformamide (20 ml). Sodium azide (650 mg) was added thereto, followed by stirring at 60° C. for 2 hr. The reaction mixture was allowed to cool to room temperature, then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=3:1). Fractions containing the target compound were concentrated under reduced pressure and the residue was dried under reduced pressure to provide the titled compound as white crystals (685 mg, 34%).

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=3:1)
  7. additionFractions containing the target compound
  8. concentrationwere concentrated under reduced pressure
  9. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-5e39d9d59a20419789728863cbe94674
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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