Sodium Azide → 2-Azido-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanone

HRID 720861Notes

Reaction equation

HRID 720861 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[O:9][C:10]([CH3:14])([CH3:13])[O:11][CH2:12][C:7]=2[CH:6]=1)=[O:4].[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N:17]([CH2:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[O:9][C:10]([CH3:14])([CH3:13])[O:11][CH2:12][C:7]=2[CH:6]=1)=[O:4])=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 11150315Ethanone, 2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-

Product 1

HCID 114023652-Azido-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanoneYield 86.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

2-Bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanone (Glaxo DE 3513885, 1985) (52 g) in DMF (300 ml) was treated with sodium azide (12.24 g) and the mixture was stirred for 2 h at 20° C. The reaction mixture was diluted with ethyl acetate and washed with water and dried (MgSO4). The solvent was removed under reduced pressure to give the title compound (39.11 g). TSP+ve 248(MH)+.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e709778a967a48198f1ccd63ef7609b8
Source dataset
uspto-grants-2006_11
Patent number
US07135600B2

Reaction notes

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