Methyl iodide → HCID 77845128, compound

HRID 1477347Notes

Reaction equation

HRID 1477347 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-7ff1c8f484414d75a0d4659f5fd49434
Source dataset
uspto-grants-2016_08
Patent number
US09403794B2

Reaction notes

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