Methyl iodide → N-[4-[2-Ethyl-4-(3-methylphenyl)-1,3-thiazol-5-YL]-2-pyridyl]-N-methylphenylacetamide

HRID 1178597Notes

Reaction equation

HRID 1178597 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[S:6][C:7]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:32])[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:18]=2)=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=2)[N:9]=1)[CH3:4].[CH3:33]I.[Cl-].[NH4+]>CS(C)=O>[CH2:3]([C:5]1[S:6][C:7]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([N:23]([CH3:33])[C:24](=[O:32])[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:18]=2)=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=2)[N:9]=1)[CH3:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10295235N-[4-[2-Ethyl-4-(3-methylphenyl)-1,3-thiazol-5-YL]-2-pyridyl]phenylacetamide

Product 1

HCID 21964193N-[4-[2-Ethyl-4-(3-methylphenyl)-1,3-thiazol-5-YL]-2-pyridyl]-N-methylphenylacetamideYield 35.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (60% paraffin dispersion, 58 mg, 1.5 mmol) was added to a solution of N-[4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-2-pyridyl]phenylacetamide (0.50 g, 1.2 mmol) in dimethyl sulfoxide (5 mL) and the mixture was stirred at room temperature for 1 hour. Methyl iodide (0.09 mL, 1.5 mmol) was added to this reaction solution and the mixture was stirred at room temperature for 1 hour. A 10% aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 7:1→4:1) and washed with hexane to obtain 0.18 g (yield 35%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 7:1→4:1)
  7. washwashed with hexane

Sources & evidence

ORD record
ord-5eeb42198d144673bc17a1c4d5d917d6
Source dataset
uspto-grants-2007_10
Patent number
US07276527B2

Reaction notes

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