Sodium Chloride → 5-Azidomethyl-3-(5-bromo-thien-2-yl)-4,5-dihydro-isoxazole

HRID 747198Notes

Reaction equation

HRID 747198 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[CH2:11][CH:10]([CH2:12]OS(C)(=O)=O)[O:9][N:8]=2)=[CH:4][CH:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[Na+]>CN(C)C=O>[N:18]([CH2:12][CH:10]1[O:9][N:8]=[C:7]([C:5]2[S:6][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:11]1)=[N+:19]=[N-:20]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 33557Sodium AzideHCID 59749454Methanesulfonic acid 3-(5-bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl ester

Product 1

HCID 179544855-Azidomethyl-3-(5-bromo-thien-2-yl)-4,5-dihydro-isoxazoleYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Methanesulfonic acid 3-(5-bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl ester (9 g, 26.4 mmol) was added to dimethyl formamide (25 ml) followed by addition of sodium azide (3.4 g, 52.8 mmol). The mixture was heated to 75° C. for five hours and then added to aqueous sodium chloride (100 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 (7.4 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-4f499e58fd1549c099e0692e1e61c043
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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