Acetonitrile → HCID 86591071, compound

HRID 2377557Notes

Reaction equation

HRID 2377557 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[N:9]3)[N:4]=[CH:3][CH:2]=1.[Cl:15][CH2:16][C:17]1[CH:24]=[CH:23][C:20](C=C)=[CH:19][CH:18]=1.[CH3:25][C:26]#N>>[Cl-:15].[CH2:16]([N+:4]1([CH:25]=[CH2:26])[C:5]2[C:14](=[C:13]3[C:8](=[CH:7][CH:6]=2)[N:9]=[CH:10][CH:11]=[CH:12]3)[CH:1]=[CH:2][CH2:3]1)[C:17]1[CH:24]=[CH:23][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 674724,7-PhenanthrolineHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 86591071HCID 86591071, compound

Procedure

A flame dried, side armed 100-mL round bottom flask, equipped with a magnetic stirring bar, was cooled under argon and charged with 4,7-phenanthroline (2.14 g, 11.86 mmols). The flask was equipped with a reflux condenser attached to an argon (g) line and charged with 4-(chloromethyl)styrene (0.905 g, 0.836 mL, 5.93 mmols) and anhydrous CH3CN (20 mL) through the side arm. The solution was heated to reflux under argon (g) for 17 h, then cooled to room temperature and precipitated with diethyl ether (30 mL). The suspension was allowed to settle and the supernatant removed via cannula. The remaining residue along with 15 mL of solvent was cannulated into a centrifuge tube, triturated with acetone (20 mL), and centrifuged (process repeated 4 times). The brownish/pink solid was triturated with diethyl ether (3×20 mL) and dried under reduced pressure. Yield: 0.376 g, 1.13 mmols (19%). 1H NMR (250 MHz, CD3OD, ppm): 5.266 (d, 1H, 11 Hz), 5.80 (d, 1H, J=17.75 Hz), 6.482 (s, 2H), 6.708 (dd, 1H, J1=11 Hz, J2=17.75 Hz), 7.374 (d, 1H, J=8 Hz), 7.496 (d, 1H, J=8 Hz) 8.00, (dd, 1H, J1=4 Hz, J2=8.5 Hz), 8.453 (dd, 1H, J1=6 Hz, J2=8.5 Hz), 8.60 (d, 1H, J=10 Hz), 8.697 (d, 1H, J=10 Hz), 9.20 (d, 1H, J=4 Hz), 9.50 (d, 1H, J=8.25 Hz), 9.65 (d, 1H, J=5.75 Hz), 10.188 (d, 1H, J=8.5 Hz). 13C NMR (62.5 MHz, CD3OD); 62.40, 121.344, 124.899, 126.023, 128.454, 129.031, 130.778, 132.161, 133.893, 134.242, 137.205, 139.848, 140.410, 140.699, 144.041, 147.976, 149.541, 154.661.

Workup

  1. customA flame dried
  2. customside armed 100-mL round bottom flask, equipped with a magnetic stirring bar
  3. temperaturewas cooled under argon
  4. customThe flask was equipped with a reflux condenser
  5. temperatureThe solution was heated
  6. temperatureto reflux under argon (g) for 17 h
  7. customprecipitated with diethyl ether (30 mL)
  8. customthe supernatant removed via cannula
  9. customThe remaining residue along with 15 mL of solvent was cannulated into a centrifuge tube
  10. customtriturated with acetone (20 mL), and centrifuged (process repeated 4 times)
  11. customThe brownish/pink solid was triturated with diethyl ether (3×20 mL)
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-8e950541546c4c2b8b671136a021a0a9
Source dataset
uspto-grants-2008_12
Patent number
US07470420B2

Reaction notes

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