Sodium Azide → HCID 16748734, compound

HRID 457574

Reaction equation

HRID 457574 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](=[O:8])[CH2:6]Br.[N-:12]=[N+:13]=[N-:14].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](=[O:8])[CH2:6][N:12]=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-one

Product 1

HCID 16748734HCID 16748734, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 20.2 g (73 mmol) of 3-bromophenacyl bromide and 5.42 g (83 mmol) of sodium azide was stirred at RT for 90 min in methanol. The solvent was removed under reduced pressure and the crude product was partitioned between ethyl acetate (200 ml) and water (100 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford the title compound (17.4 g, 99%) as a light yellow solid. 1H NMR (400 MHz, d6-DMSO): δ 8.10 (d, J=1.0, 1H), 7.90–7.97 (m, 2H), 7.22 (t, J=7.9, 1H), 4.93 (s, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was partitioned between ethyl acetate (200 ml) and water (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04496d367c7b4f678864836d4b3ee3b1
Source dataset
uspto-grants-2007_03
Patent number
US07189712B2

Linked notes

Loading…