Methyl iodide → HCID 86638784, compound

HRID 1618872Notes

Reaction equation

HRID 1618872 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[I:18][CH3:19]>C(#N)C>[I-:18].[N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]=[CH:11][C:12]2[CH:13]=[CH:14][N+:15]([CH3:19])=[CH:16][CH:17]=2)=[CH:8][CH:9]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 72536702HCID 72536702, compound

Product 1

HCID 86638784HCID 86638784, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 100 mL round bottom flask equipped with a stirbar and covered with foil, 4-[2-(4-azido-phenyl)-vinyl]-pyridine (0.57 g, 2.56 mmol) was mixed with iodomethane (0.95 g, 6.7 mmol) in acetonitrile (20 mL) and stirred at room temperature for 36 hrs. A precipitate had formed and TLC showed a single spot, so the solution was placed in the refrigerator for 30 minutes and then filtered, rinsing with diethyl ether. The product was collected as a yellow powder (0.482 g). Diethyl ether was added to the filtrates and then placed in the refrigerator for 2 his. Orange/brown crystals formed which were collected by suction filtration (0.15 g). The total amount of product collected was 0.63 g (68% yield). mp 166.2-168.0° C. 1H NMR (400 MHz, DMSO-d6) δ 8.86 (d, J=6.9 Hz, 2H), 8.20 (d, J=6.9 Hz, 2H), 8.01 (d, J=16.4 Hz, 1H), 7.80 (ddd, J=1.8, 2.6, 8.5 Hz, 2H), 7.49 (d, J=16.4 Hz, 1H), 7.26 (ddd, J=1.8, 2.6, 8.5 Hz, 2H), 4.26 (s, 3H). 13C NMR (100 MHz, DMSO-d6) 152.89, 145.56, 141.80, 140.08, 132.54, 130.31, 123.90, 123.28, 120.37, 47.39. λmaxCH3CN 373 nm (ε 4.07×104). IR νmax (cm−1) 2118 (N3).

Workup

  1. customIn a 100 mL round bottom flask equipped with a stirbar
  2. customA precipitate had formed
  3. waitso the solution was placed in the refrigerator for 30 minutes
  4. filtrationfiltered
  5. washrinsing with diethyl ether
  6. customThe product was collected as a yellow powder (0.482 g)
  7. additionDiethyl ether was added to the filtrates
  8. customOrange/brown crystals formed which
  9. filtrationwere collected by suction filtration (0.15 g)
  10. customThe total amount of product collected

Sources & evidence

ORD record
ord-0ab4dd7041434c17aebb039d1166490e
Source dataset
uspto-grants-2014_07
Patent number
US08772048B2

Reaction notes

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