Lithium azide → HCID 19781831, compound

HRID 257844Notes

Reaction equation

HRID 257844 reaction equation
Br[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1.[N-:22]=[N+:23]=[N-:24].[Li+]>CS(C)=O>[N:22]([CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)=[N+:23]=[N-:24]

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 19385740Methyl 2-(4-bromomethylphenoxy)-2-(2-chlorophenyl)acetate

Product 1

HCID 19781831HCID 19781831, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A concentrated stirred solution of the product of Step D in anhydrous dimethylsulfoxide (DMSO) is treated at ambient temperature with lithium azide (25% excess) portionwise. The mixture is then stirred at ambient temperature under protection from moisture for about 1 hour, or until TLC indicates complete reaction. The mixture is then partitioned between ether (or ethyl acetate) and water. The organic phase is washed repeatedly with H2O, then dried over MgSO4, filtered, and concentrated. The residue may be purified by chromatography on silica gel.

Workup

  1. customreaction
  2. customThe mixture is then partitioned between ether (or ethyl acetate) and water
  3. washThe organic phase is washed repeatedly with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue may be purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1b82ed8b64124b7ba5b4aa181854c014
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Reaction notes

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