Benzyl mercaptan → 5-(2-Benzylthio-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazole

HRID 2212357Notes

Reaction equation

HRID 2212357 reaction equation
[H-].[Na+].[C:3]1([CH2:9][SH:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:12]1[CH:17]=[C:16]([C:18]2[S:22][C:21]([C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)=[N:20][C:19]=2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[CH:15]=[CH:14][N:13]=1.[OH-].[Na+]>CCCCCC.CN(C)C=O>[CH2:9]([S:10][C:12]1[CH:17]=[C:16]([C:18]2[S:22][C:21]([C:23]3[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:30])=[O:31])=[CH:27][CH:28]=3)=[N:20][C:19]=2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[CH:15]=[CH:14][N:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 102739295-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazole

Product 1

HCID 219642205-(2-Benzylthio-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazoleYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

After sodium hydride (60% paraffin dispersion, 0.13 g, 3.2 mmol) was washed with hexane twice, it was suspended in N,N-dimethylformamide (15 mL). Phenylmethanethiol (0.35 mL, 3.0 mmol) was added to this suspension and stirred for 10 minutes. A solution of 5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazole (0.49 g, 1.2 mmol) in N,N-dimethylformamide (5 mL) was added to this mixture and stirred for 1 hour. An 8N aqueous solution of sodium hydroxide was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate, and the extract was washed with water. This extract was dried and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1) to obtain 0.48 g (yield 79%).

Workup

  1. stirringstirred for 1 hour
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. customThis extract was dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1)
  7. customto obtain 0.48 g (yield 79%)

Sources & evidence

ORD record
ord-3b1ebd6d92da4ff3a4beef72afe82f00
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

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