Sodium Azide → (E)-4-(4-azidobut-1-enyl)-1,2-dichlorobenzene

HRID 1848369Notes

Reaction equation

HRID 1848369 reaction equation
CS(O[CH2:6][CH2:7]/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)(=O)=O.[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C=O)C.CCOC(C)=O>[N:18]([CH2:6][CH2:7]/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)=[N+:19]=[N-:20]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86728171(E)-4-(3,4-dichlorophenyl)but-3-enyl methanesulfonate

Product 1

HCID 86728172(E)-4-(4-azidobut-1-enyl)-1,2-dichlorobenzeneYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 2C (1.3 g, 4.4 mmol) in DMF (7 mL) was added NaN3 (0.86 g, 13 mmol). The reaction mixture was stirred at rt for 16 h. The reaction mixture was diluted with EtOAc (100 mL). The organic layer was washed with 10% aqueous LiCl solution (3×200 mL), dried over Na2SO4 and dried in vacuo. The product was isolated by silica gel chromatography to obtain 570 mg (87% yield) of Intermediate 2D. HPLC/MS (Method C)RT=4.02 min, [M+Na]+ 263.2.

Workup

  1. washThe organic layer was washed with 10% aqueous LiCl solution (3×200 mL)
  2. dry with materialdried over Na2SO4
  3. customdried in vacuo
  4. customThe product was isolated by silica gel chromatography

Sources & evidence

ORD record
ord-254b620c16f8478fb2c6143a0616b293
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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