Sodium Azide → HCID 14987327, compound

HRID 653890Notes

Reaction equation

HRID 653890 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([O:17][CH3:18])=[O:16])=[CH:5][CH:4]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C>[N:19]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([O:17][CH3:18])=[O:16])=[CH:5][CH:4]=1)=[N+:20]=[N-:21]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

Product 1

HCID 14987327HCID 14987327, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromomethyl-2'-methoxycarbonylbiphenyl (150 g, 0.49 mol) in dry DMF (500 ml) was added NaN3 (80 g, 1.23 mol, 2.5 eq). The mixture was stirred at room temperature overnight (ca. 18 hours), filtered, and the filtrate was partitioned between ethyl acetate and H2O (500 ml each). The organic phase was washed twice more with H2O, once with saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate before being filtered and concentrated to leave 111.3 g (85%) of a yellow oil, used in the following step without further purification. NMR (CDCl3, TMS, δ) 7.9-7.1 (m, 8H), 4.35 (s, 2H), 3.55 (s, 3H) IR Vmax 2487 cm-1.

Workup

  1. filtrationfiltered
  2. customthe filtrate was partitioned between ethyl acetate and H2O (500 ml each)
  3. washThe organic phase was washed twice more with H2O, once with saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationbefore being filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c1518471f14540cdb429921d844a8eb5
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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