Sodium Chloride → HCID 17954492, compound

HRID 747188Notes

Reaction equation

HRID 747188 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][C:3]=1[F:19].[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[Na+]>CN(C)C=O>[N:20]([CH2:13][CH:11]1[O:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([F:19])[CH:4]=2)[CH2:12]1)=[N+:21]=[N-:22]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 33557Sodium AzideHCID 59749462HCID 59749462, compound

Product 1

HCID 17954492HCID 17954492, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Methanesulfonic acid 3-(4-bromo-3-fluoro-phenyl)-4,5-dihydro-isoxazol-5-ylmethyl ester (38.6 g, 111.9 mmol) was added to dimethyl formamide (100 ml) followed by addition of sodium azide (14.5 g, 223.8 mmol). The mixture was heated to 75° C. for five hours and then added to aqueous sodium chloride (200 ml) followed by extraction with ethyl acetate (3×200 ml). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to yield the desired product (31 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate (3×200 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72f9bd4fd76741f69a218a08a1065bfc
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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