Lithium azide → HCID 19781831, compound
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
Product 1
Reagents, catalysts & solvents 1
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.