Methyl iodide → HCID 11393176, compound

HRID 1766305Notes

Reaction equation

HRID 1766305 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:22])[C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH3:21])=[CH:15][CH:14]=3)=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[CH3:25]I>CN(C=O)C>[CH3:25][N:11]([C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH:7]=1)[C:12](=[O:22])[C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH3:21])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11335895HCID 11335895, compound

Product 1

HCID 11393176HCID 11393176, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-methylbenzothiazol-5-yl)-4-propylbenzamide (130 mg, 0.4 mmol) in DMF (5 mL) was added sodium hydride (17 mg, 0.44 mmol), followed by methyl iodide (85 mg, 059 mmol). The mixture was stirred at rt overnight, partitioned between water and ethyl acetate. The organic phase was washed with brine, dried over sodium sulphate and concentrated to give a residue that wad purified with flash chromatography (ethyl acetate-hexane gradient elution). A thick syrup (41 mg, 26% was obtained. 1H NMR (400 MHz, CDCl3): δ 7.61-7.79 (3H, m, ArH), 7.22-7.26 (2H, m, ArH), 6.92-7.02 (2H, m, ArH), 3.54 (3H, s, CH3) 2.81 (3H, s, CH3), 2.45 (2H, t J=7.4 Hz, CH2) 1.52 (2H, m, CH2), 0.83 (3H, t, .J=7.4 Hz, CH3); FAB-MS 325 (MH+); FAB-HRMS calcd for C19H21N2OS (MH+) 325.1375, found 325.1992.

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customto give a residue that
  6. customwad purified with flash chromatography (ethyl acetate-hexane gradient elution)
  7. customA thick syrup (41 mg, 26% was obtained

Sources & evidence

ORD record
ord-c825fd3a53c746eba4922a83e8b65f28
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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