Methyl iodide → HCID 77845128, compound

HRID 1774083Notes

Reaction equation

HRID 1774083 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]1[C:20]2[CH:19]=[CH:18][C:17](/[CH:21]=[CH:22]/[C:23]3[C:24]4[C:29]([N:30]=[C:31]5[C:36]=3[CH:35]=[CH:34][CH:33]=[CH:32]5)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.[CH3:37][I:38]>C(#N)C>[I-:38].[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]1[C:20]2[CH:19]=[CH:18][C:17](/[CH:21]=[CH:22]/[C:23]3[C:36]4[C:31]([N+:30]([CH3:37])=[C:29]5[C:24]=3[CH:25]=[CH:26][CH:27]=[CH:28]5)=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86672680HCID 86672680, compound

Product 1

HCID 77845128HCID 77845128, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 12 (0.20 g, 0.4 mmol) and methyl iodide (0.57 g, 4 mmol) in acetonitrile (8 mL) was heated to 100° C. in sealed tube for 24 h. After cooling down to room temperature, the solvent was removed and the resulting mixture was purified by precipitation from methanol and ethyl acetate to afford SAM (0.15 g) in 61% yield. 1H NMR (400 MHz, CDCl3) δ 8.74 (d, J=8.0 Hz, 2H), 8.49 (s, 1H), 8.46 (d, J=8.8 Hz, 2H), 8.31 (d, J=16 Hz, 1H), 8.26 (t, J=8.0 Hz, 2H), 8.10 (d, J=8.0 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H), 7.83 (t, J=7.2 Hz, 2H), 7.51 (d, J=8.4 Hz, 1H), 7.46 (t, J=6.4 Hz, 2H), 7.44 (d, J=16 Hz, 1H), 7.20 (t, J=6.4 Hz, 1H), 4.82 (s, 3H), 4.46 (t, J=6.0 Hz, 2H), 3.88 (t, J=6.0 Hz, 2H), 3.55-3.53 (m, 2H), 3.44-3.42 (m, 2H), 3.30 (s, 3H). 13C NMR (400 MHz, CDCl3) δ 157.9, 149.5, 141.8, 140.5, 140.1, 137.8, 129.3, 127.4, 126.9, 126.5, 126.2, 123.9, 123.2, 122.1, 121.2, 121.1, 119.9, 117.9, 117.4, 109.4, 109.0, 71.7, 70.6, 69.0, 58.9, 43.3, 39.5. HRMS (MALDI-TOF) m/z Calcd for C33H31N2O2+ 487.2380 Found 487.2387 [M]+.

Workup

  1. customthe solvent was removed
  2. customthe resulting mixture was purified by precipitation from methanol and ethyl acetate
  3. customto afford SAM (0.15 g) in 61% yield

Sources & evidence

ORD record
ord-37419785f50b4893b607a7efcb170fa8
Source dataset
uspto-grants-2016_02
Patent number
US09255933B2

Reaction notes

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