Sodium Azide → HCID 14987327, compound

HRID 2249215Notes

Reaction equation

HRID 2249215 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[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[C:10]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[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, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4'-bromomethylbiphenyl-2-carboxylate (5.0 g, 16.4 mmol) in DMF (40 ml) was added sodium azide (2.7 g, 41 mmol). The mixture was stirred overnight at room temperature, filtered, and the filtrate was partitioned between water and ethyl acetate (100 ml). The aqueous phase was extracted once more with ethyl acetate (100 ml) and the combined organic phase was washed with water (3×100 ml) and saturated aqueous sodium chloride (100 ml) before being dried (MgSO4), filtered and concentrated to an oily residue (3.9 g) which was used in the subsequent reaction without further purification: NMR (200 MHz; CDCl3,TMS)δ: 7.9-7.2(m,8H), 4.37(s,2H), and 3.60(s,3H).

Workup

  1. filtrationfiltered
  2. customthe filtrate was partitioned between water and ethyl acetate (100 ml)
  3. extractionThe aqueous phase was extracted once more with ethyl acetate (100 ml)
  4. washthe combined organic phase was washed with water (3×100 ml) and saturated aqueous sodium chloride (100 ml)
  5. dry with materialbefore being dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to an oily residue (3.9 g) which
  8. customwas used in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-9f0a3e117cbd46f08ef6d26131590d60
Source dataset
uspto-grants-1991_08
Patent number
US05043349

Reaction notes

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