Water → HCID 21913014, compound

HRID 1008064Notes

Reaction equation

HRID 1008064 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:25]2[C:24]([CH3:26])=[C:23]([CH3:27])[N:22]=[C:21]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:20]=2[N:19]=[C:18]1[CH2:35][CH2:36][CH3:37].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[C:25]3[C:24]([CH3:26])=[C:23]([CH3:27])[N:22]=[C:21]([O:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:20]=3[N:19]=[C:18]2[CH2:35][CH2:36][CH3:37])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7815p-ChlorothiophenolHCID 24758Sodium hydrideHCID 21912893HCID 21912893, compound

Product 1

HCID 21913014HCID 21913014, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of 4-chlorobenzenethiol (868 mg, 6.00 mmol) in DMF (5 mL) was added to a mixture of sodium hydride (60% dispersion, 240 mg, 6.00 mmol) in DMF (15 mL); the reaction became homogeneous and was stirred for 15 minutes. Solid 1-(5-chloropentyl)-6,7-dimethyl-4-phenoxy-2-propyl-1H-imidazo[4,5-c]pyridine (1.93 g, 5.00 mmol) was added in small amounts, and the reaction was stirred for 1.5 hours. Water (25 mL) was added, and the resulting solution was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with water (5×30 mL) and brine (2×10 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a colorless oil, which crystallized overnight. The solid was dried for three hours under high vacuum to provide 2.58 g of 1-[5-(4-chlorophenylsulfanyl)pentyl]-6,7-dimethyl-4-phenoxy-2-propyl-1H-imidazo[4,5-c]pyridine as a white solid.

Workup

  1. stirringthe reaction was stirred for 1.5 hours
  2. extractionthe resulting solution was extracted with ethyl acetate (3×50 mL)
  3. washThe combined extracts were washed with water (5×30 mL) and brine (2×10 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide a colorless oil, which
  8. customcrystallized overnight
  9. customThe solid was dried for three hours under high vacuum

Sources & evidence

ORD record
ord-d09992988d6b46bc8b5be98a181bd4ad
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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