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

HRID 1987259Notes

Reaction equation

HRID 1987259 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=O)C>[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 DMF (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 (2×100 mL). The combined organic extracts were washed with water, dried over MgSO4, 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 (2×100 mL)
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over MgSO4
  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-e68b39c42ea549eea67e1022f6c59a46
Source dataset
uspto-grants-2009_06
Patent number
US07550489B2

Reaction notes

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