Thiophenol → HCID 21912920, compound

HRID 1008024Notes

Reaction equation

HRID 1008024 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24]2[C:23]([CH3:25])=[C:22]([CH3:26])[N:21]=[C:20]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:19]=2[N:18]=[C:17]1[CH3:34]>CN(C)C=O>[CH3:34][C:17]1[N:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:24]2[C:23]([CH3:25])=[C:22]([CH3:26])[N:21]=[C:20]([O:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:19]=2[N:18]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 21914058HCID 21914058, compound

Product 1

HCID 21912920HCID 21912920, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Benzenethiol (2.42 mL, 23.6 mmol) was added dropwise to a suspension of sodium hydride (0.944 g of 60%, 23.6 mmol) in anhydrous N,N-dimethylformamide (50 mL) and stirred until a clear solution was obtained. A solution of 1-(5-chloropentyl)-2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridine (6.5 g, 18.2 mmol) in anhydrous N,N-dimethylformamide (50 mL) was added dropwise. The reaction mixture was stirred at ambient temperature for 2 hours, then it was quenched with water and extracted with ethyl acetate (300 mL). The extract was washed with water (5×75 mL), dried over magnesium sulfate and then concentrated under reduced pressure to provide 7.20 g of 2,6,7-trimethyl-4-phenoxy-1-[5-(phenylthio)pentyl]-1H-imidazo[4,5-c]pyridine.

Workup

  1. customwas obtained
  2. stirringThe reaction mixture was stirred at ambient temperature for 2 hours
  3. customit was quenched with water
  4. extractionextracted with ethyl acetate (300 mL)
  5. washThe extract was washed with water (5×75 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f8a6dc6d6121485f980728c08e9f7b7a
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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