Methyl iodide → HCID 50900632, compound

HRID 1921921Notes

Reaction equation

HRID 1921921 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9]1[C:10]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])=[CH:11][CH:12]=[CH:13][CH:14]=1.[CH3:26]I>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9]1[C:10]([N:15]([CH3:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 50900631HCID 50900631, compound

Product 1

HCID 50900632HCID 50900632, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4 (0.405 g, 1.14 mmol) was dissolved in 4 mL of dimethylformamide (DMF) and added to KH (0.46 g, 3.42 mmol). The mixture was stirred at room temperature for 10 min. To this, MeI (0.4 mL, 5.7 mmol) was added dropwise. The reaction was allowed to stir at room temperature for 30 min. The reaction was then quenched with deionized H2O and extracted 3 times with 15 mL dichloromethane. The organic layers were combined and washed 3 times with 15 mL of H2O, and 3 times with 15 mL of brine. The organic layers were dried with MgSO4, and solvent was removed under reduced pressure to give the desired product as a yellow powder without further purification (0.362 g, 86% yield). 1H NMR (300 MHz, CDCl3) δ 7.63 (1H, dd, J=8.0, 1.7 Hz), 7.36 (1H, ddd, J=8.8, 7.3, 1.8 Hz), 7.29-7.19 (2H, m), 7.12 (1H, dd. J=8.2, 1.7 Hz), 7.07-6.92 (5H, m), 6.88 (1H, ddd, J=8.2, 7.3, 1.2 Hz), 6.81 (1H, dd, J=7.8, 1.2 Hz), 3.32 (3H, s), 3.27 (3H, s); 13C (75 MHz, CDCl3) δ 146.5 (q), 143.5 (q), 142.1 (q), 138.8 (q), 132.7 (t), 131.0 (t), 128.7 (q), 127.6 (t), 126.2 (t), 124.2 (t), 124.1 (t), 123.7 (t), 123.1 (t), 120.4 (t), 118.8 (t), 38.5, 38.1.

Workup

  1. additionadded to KH (0.46 g, 3.42 mmol)
  2. stirringto stir at room temperature for 30 min
  3. customThe reaction was then quenched with deionized H2O
  4. extractionextracted 3 times with 15 mL dichloromethane
  5. washwashed 3 times with 15 mL of H2O, and 3 times with 15 mL of brine
  6. dry with materialThe organic layers were dried with MgSO4, and solvent
  7. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-7d6f75d8b4ec467dbc8bd99f9a9d71e1
Source dataset
uspto-grants-2012_05
Patent number
US08173803B2

Reaction notes

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