Sodium Azide → HCID 90411866, compound

HRID 1427734Notes

Reaction equation

HRID 1427734 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)=[O:13])=[CH:8][CH:7]=1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[N:21]([CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)=[O:13])=[CH:8][CH:7]=1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 90411367HCID 90411367, compound

Product 1

HCID 90411866HCID 90411866, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

A solution of (4-(3-bromopropoxy)phenyl)(4-Iodophenyl)methanone (50.0 g, 112 mmol), and sodium azide (10.2 g, 157 mmol) was dissolved in DMF (300 ml). The reaction was heated to 45° C. and left to stir overnight. Upon completion, the reaction mixture was filtered to remove sodium salt and concentrated under reduced pressure. The crude was then further extracted with chloroform, the organic layer was washed with brine, and dried over anhydrous sodium sulfate to afford 40.3 g (88.0% yield) of (4-(3-azidopropoxy)phenyl)(4-iodophenyl)methanone as grey solid.

Workup

  1. waitleft
  2. filtrationUpon completion, the reaction mixture was filtered
  3. customto remove sodium salt
  4. concentrationconcentrated under reduced pressure
  5. extractionThe crude was then further extracted with chloroform
  6. washthe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-2ca4061895b54a0cb30e257da22fc5b8
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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