Sodium Azide → HCID 59811013, compound
Reaction equation
[CH:1]1[CH:5]=[C:4]([C:6]([CH2:8][CH2:9][CH2:10]Cl)=[O:7])[S:3][CH:2]=1.[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[N:12]([CH2:10][CH2:9][CH2:8][C:6]([C:4]1[S:3][CH:2]=[CH:1][CH:5]=1)=[O:7])=[N+:13]=[N-:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 4-chloro-2′-butyrothienone (3.0 g, 15.9 mmol) and sodium azide (2.07 g, 31.8 mmol) in DMF (50 mL) was stirred at 70° C. for 1.5 h. The reaction mixture was then partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was washed with water (100 mL), saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL) and dried over sodium sulfate. Removal of the solvent in vacuum provided the title compound (2.58 g, 83% yield). MS m/e 218; HPLC retention time 0.85 min (Method B).
Workup
- customThe reaction mixture was then partitioned between ethyl acetate (200 mL) and water (200 mL)
- washThe organic layer was washed with water (100 mL), saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL)
- dry with materialdried over sodium sulfate
- customRemoval of the solvent in vacuum
Sources & evidence
- ORD record
- ord-41d2f3ba75084204b983156a0868ea89
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432271B2
Reaction notes
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