Sodium Iodide → 1-But-3-ynyl-1H-[1,2,3]triazole
Reaction equation
[OH-].[Na+].[I-].[Na+].[NH:5]1[CH:9]=[CH:8][N:7]=[N:6]1.CS([O-])(=O)=O.[CH3:15][C:16](O)([CH2:18][CH3:19])C>>[CH2:19]([N:5]1[CH:9]=[CH:8][N:7]=[N:6]1)[CH2:18][C:16]#[CH:15]Participants
Procedure
A suspension of NaOH (37.86 g, 946.5 mmol), sodium iodide (94.65 g, 631.5 mmol) and 1H-[1,2,3]triazole (61.03 g, 883.6 mmol) in 2-methyl-2-butanol (750 mL) was refluxed for 1 h under an inert atmosphere. After cooling to room temperature the methane sulfonate (94.18 g, 631.2 mmol) was added within 5 minutes. The resulting suspension was then heated to reflux for 3 h, cooled to room temperature and concentrated in vacuo at 45° C. Water (500 mL) and dichloro methane (1 L) were added and the organic phase was separated, dried over sodium sulfate and the volatiles removed at 30° C. The residue was distilled at 1 mmHg. A forerun was collected at 20–70° C. The main fraction distilled at 123–129° C. as a colorless, turbid liquid. After filtration over Celite 1-but-3-ynyl-1H-[1,2,3]triazole was obtained as a colorless liquid (29.77 g, 38.9%).
Workup
- temperaturewas refluxed for 1 h under an inert atmosphere
- additionwas added within 5 minutes
- temperatureThe resulting suspension was then heated
- temperatureto reflux for 3 h
- concentrationconcentrated in vacuo at 45° C
- additionWater (500 mL) and dichloro methane (1 L) were added
- customthe organic phase was separated
- dry with materialdried over sodium sulfate
- customthe volatiles removed at 30° C
- distillationThe residue was distilled at 1 mmHg
- customA forerun was collected at 20–70° C
- distillationThe main fraction distilled at 123–129° C. as a colorless, turbid liquid
- filtrationAfter filtration over Celite 1-but-3-ynyl-1H-[1,2,3]triazole
Sources & evidence
- ORD record
- ord-38e0077376554273a8fd69db29110a1a
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07205326B2
Reaction notes
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