Water → 1-(3-Azido-2-phenylbutyl)-4-chlorobenzene

HRID 30350Notes

Reaction equation

HRID 30350 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10](OS(C)(=O)=O)[CH3:11])=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+].O>CN(C)C=O>[N:23]([CH:10]([CH:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:11])=[N+:24]=[N-:25]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 22270384HCID 22270384, compound

Product 1

HCID 222704481-(3-Azido-2-phenylbutyl)-4-chlorobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-(4-chlorophenyl)-2-methanesulfonyloxy-3-phenylbutane (Step F, 12 g, 34 mmol) in dimethylformamide (50 mL) was added sodium azide (11 g, 0.17 mol). After stirring at 120° C. for 1 h, the reaction mixture was poured into water (200 mL), and the product was extracted with ether (2 times 100 mL). The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated to dryness, and the residue was purified on a silica gel column eluting with hexane to give the title compound.

Workup

  1. extractionthe product was extracted with ether (2 times 100 mL)
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customthe residue was purified on a silica gel column
  7. washeluting with hexane

Sources & evidence

ORD record
ord-9a27e9b11d0b4cf9b1a0b55333385f2a
Source dataset
uspto-grants-2008_09
Patent number
US07423067B2

Reaction notes

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