Sodium Chloride → 5-Azidomethyl-3-(4-bromo-phenyl)-4,5-dihydro-isoxazole

HRID 747183Notes

Reaction equation

HRID 747183 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13]OS(C)(=O)=O)[O:10][N:9]=2)=[CH:4][CH:3]=1.[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[Na+]>CN(C)C=O>[N:19]([CH2:13][CH:11]1[O:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:12]1)=[N+:20]=[N-:21]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 33557Sodium AzideHCID 18698757[3-(4-Bromophenyl)-4,5-dihydroisoxazol-5-yl]methyl methanesulfonate

Product 1

HCID 179544685-Azidomethyl-3-(4-bromo-phenyl)-4,5-dihydro-isoxazoleYield 112.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Methanesulfonic acid 3-(4-bromo-phenyl)-4,5-dihydro-isoxazol-5-ylmethyl ester (55 g, 164.2 mmol) was added to dimethyl formamide (200 ml) followed by addition of sodium azide (21.4 g, 328.4 mmol). The mixture was heated to 75° C. for six hours and then added to aqueous sodium chloride (300 ml) followed by extraction with gethyl acetate (3×300 ml). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to yield the desired product (52 g).

Workup

  1. extractionfollowed by extraction with gethyl acetate (3×300 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8cab888258b4224a137730ce68e6483
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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