Methyl iodide → HCID 44553220, compound

HRID 1254033Notes

Reaction equation

HRID 1254033 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:10]=[C:11]([CH3:24])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.I[CH3:26].[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:10]([CH3:26])[C:11]([CH3:24])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66986382HCID 66986382, compound

Product 1

HCID 44553220HCID 44553220, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the product of Step 4 (0.38 g, 0.96 mmol) and iodomethane (1.0 mL, 1M solution in THF, 1.0 mmol) in THF (5 mL) at 5° C. under argon was added NaH (60% in mineral oil, 0.040 g, 1.0 mmol). After stirring at RT for 16 h, the reaction was partitioned between CH2Cl2 (10 mL) and H2O (20 mL). The organic layer was separated, washed with H2O, brine, dried with anhydrous Na2SO4 and concentrated. The residue was purified by crystallization from EtOAc/hexane to give the title compound. 1H NMR (400 MHz, CDCl3): 2.52 (3H, s), 3.03 (3H, s), 3.51 (3H, s), 6.91-6.99 (2H, m), 7.21-7.29 (2H, m), 7.88-7.94 (2H, m), 8.21-8.27 (2H, m). LC-MS: m/z 393.0 [M+H]+

Workup

  1. customthe reaction was partitioned between CH2Cl2 (10 mL) and H2O (20 mL)
  2. customThe organic layer was separated
  3. washwashed with H2O, brine
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by crystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-c12d527e88ed4071a4879ab64f7b4cbd
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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