Iodine → 9-(3-Iodoprop-2-YN-1-YL)-9H-carbazole
Reaction equation
[CH2:1]([N:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:2]#[CH:3].O.[OH-].[Na+].[I:20]I>CO.O1CCCC1>[I:20][C:3]#[C:2][CH2:1][N:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2Participants
Conditions
- Temperature
- 4 °C
Procedure
Procedure: To a solution of 1.23 g (0.006 mol) of N-(2-propynyl)carbazole in 19.2 mL of methanol 4.8 mL of water and 0.48 g of NaOH were added while stirring at 4° C. Addition of 6 mL of tetrahydrofurane (THF) to the turbid suspension resulted in a homogeneous solution. Then 1.52 g of crystalline iodine was added portion-wise. After 10 min of stirring the iodine color disappeared and the product started to separate as a dense white precipitate. Over 8 hrs of stirring at room temperature the product was filtered, washed with distilled water and air dried. 1.25 g (Yield 65%) of N-(3-Iodo-2-propynyl)carbazole has been obtained as crystals having m.p. 151-152° C. When applied onto a printing paper and analyzed according to Example 1, the compound gave an intense NIR FT-Raman spectrum in some features similar, but clearly not identical, to that shown in FIG. 1(A) for copper phenylacetylide (exemplary Compound #26 of the invention).
Workup
- customresulted in a homogeneous solution
- customto separate as a dense white precipitate
- stirringOver 8 hrs of stirring at room temperature the product
- filtrationwas filtered
- washwashed with distilled water and air
- customdried
Sources & evidence
- ORD record
- ord-961837d824bb4ac79ec35c2f209cff74
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06610351B2
Reaction notes
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