Methyl iodide → HCID 49806031, compound

HRID 241206Notes

Reaction equation

HRID 241206 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]4[CH:31]=[CH:30][C:25]5[NH:26][C:27](=[S:29])[NH:28][C:24]=5[CH:23]=4)[CH:20]=[CH:21][C:15]=3[O:14][CH2:13][CH2:12]2)=[CH:3][CH:2]=1.[C:32](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C)C=O>[CH3:32][S:29][C:27]1[NH:28][C:24]2[CH:23]=[C:22]([C:19]3[CH:20]=[CH:21][C:15]4[O:14][CH2:13][CH2:12][N:11]([C:4]5[C:5]6[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=6)[N:1]=[CH:2][CH:3]=5)[CH2:17][C:16]=4[CH:18]=3)[CH:31]=[CH:30][C:25]=2[N:26]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86647857HCID 86647857, compound

Product 1

HCID 49806031HCID 49806031, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 5-(4-quinolin-4-yl-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-dihydro-2H-benzimidazole-2-thione (355 mg, 0.84 mmol), potassium carbonate (578 mg, 4.18 mmol), and methyl iodide (119 mg, 0.84 mmol) in dimethylformamide (5 mL) was stirred at room temperature for 1 h. Ethyl acetate (100 mL) was added, and the organic layer was washed with water (2×20 mL), 5% aqueous lithium chloride (2×20 mL), and brine (20 mL), dried over sodium sulfate, filtered and concentrated. Column chromatography on silica (dichloromethane/methanol 95:5) provided the title Compound (220 mg, 60% yield) as a brown solid. 1H NMR (400 MHz, CDCl3): 8.71 (d, 1H), 8.09 (m, 2H), 7.66 (m, 1H), 7.57-7.42 (m, 5H), 7.17 (d, 1H), 6.98 (d, 1H), 4.54 (s, 2H), 4.36 (m, 2H), 3.84 (m, 2H), 2.82 (s, 3H); MS (EI) for C26H22N4OS: 439 (MH+).

Workup

  1. washthe organic layer was washed with water (2×20 mL), 5% aqueous lithium chloride (2×20 mL), and brine (20 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ba0ce4e64f6d42aea923dd61692c8caa
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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