Thionyl Chloride → HCID 23456654, compound
Reaction equation
[C:1]([C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][N:7]=1)([O:3][CH2:4][CH3:5])=[O:2].S(Cl)([Cl:17])=O>>[C:1]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([Cl:17])=[O:11])=[CH:8][N:7]=1)([O:3][CH2:4][CH3:5])=[O:2]Participants
3
Procedure
The starting material is prepared as follows: The suspension of 10 g of 6-carbethoxynicotinic acid in 40 ml of thionyl chloride is refluxed for 2 hours and evaporated. The residue is suspended in toluene and the mixture again taken to dryness. Another such cycle is repeated to yield the pure 6-carbethoxynicotinoyl chloride. It is dissolved in 150 ml of acetone and the solution cooled in an ice bath to 10°. 4.2 g of sodium azide, dissolved in 20 ml of water, are added dropwise to the acetone solution, whereupon a solid separates after several minutes. The mixture is stirred for 2 hours in the ice bath, then 150 ml of ice water are added and the solid is collected and washed with ice water, to yield the 6-carbethoxynicotinoyl azide.
Workup
- customThe starting material is prepared
- temperatureis refluxed for 2 hours
- customevaporated
Sources & evidence
- ORD record
- ord-dff342a2bab44d689091f02fbe69b6b8
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04273779
Reaction notes
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