Sodium methanethiolate → HCID 21913991, compound

HRID 1352564Notes

Reaction equation

HRID 1352564 reaction equation
[CH3:1][S-:2].[Na+].Cl[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:17]([CH3:19])=[C:16]([CH3:20])[N:15]=[C:14]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:13]=2[N:12]=[C:11]1[CH3:28]>CN(C)C=O>[CH3:28][C:11]1[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][S:2][CH3:1])[C:18]2[C:17]([CH3:19])=[C:16]([CH3:20])[N:15]=[C:14]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:13]=2[N:12]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 21914058HCID 21914058, compound

Product 1

HCID 21913991HCID 21913991, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium thiomethoxide (1.5 g, 21 mmol) was added to a solution of 1-(5-chloropentyl)-2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridine (7.00 g, 19 mmol) in anhydrous N,N-dimethylformamide (80 mL). The reaction mixture was stirred at ambient temperature for 1.5 hours, then it as quenched with water and extracted with ethyl acetate (250 mL). The extract was washed with water (5×50 mL), dried over magnesium sulfate and then concentrated under reduced pressure to provide 6.73 g of 2,6,7-trimethyl-1-[5-(methylthio)pentyl]-4-phenoxy-1H-imidazo[4,5-c]pyridine.

Workup

  1. customit as quenched with water
  2. extractionextracted with ethyl acetate (250 mL)
  3. washThe extract was washed with water (5×50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-49d3cab0f4e7427e8abfabe409bfca42
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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