Sodium methanethiolate → 8-(2,6-Dimethylbenzylamino)-3-methyl-2-methylsulfanylmethyl-imidazo[1,2-a]pyridine

HRID 1006670Notes

Reaction equation

HRID 1006670 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[C:10]([NH:11][CH2:12][C:13]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:20])=[CH:9][CH:8]=[CH:7][N:6]2[C:21]=1[CH3:22].[CH3:23][S-:24].[Na+]>C(#N)C>[CH3:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=1[CH2:12][NH:11][C:10]1[C:5]2[N:6]([C:21]([CH3:22])=[C:3]([CH2:2][S:24][CH3:23])[N:4]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 226726282-Chloromethyl-8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine

Product 1

HCID 226726258-(2,6-Dimethylbenzylamino)-3-methyl-2-methylsulfanylmethyl-imidazo[1,2-a]pyridineYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-chloromethyl-8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine (0.2 g, 0.64 mmol) and sodium methanethiolate (0.1 g, 1.3 mmol) were added to acetonitrile (10 ml) and stirred for 4 h. at room temperature. The solvent was evaporated under reduced pressure and to the residue were added methylene chloride and water. The organic layer was separated, dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using diethyl ether:petroleum ether (1:2) as eluent and crystallization from diethyl ether:petroleum ether (1:2) gave 0.05 g (24%) of the desired product.

Workup

  1. customThe solvent was evaporated under reduced pressure and to the residue
  2. additionwere added methylene chloride and water
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customPurification of the residue by column chromatography on silica gel
  7. customcrystallization from diethyl ether:petroleum ether (1:2)

Sources & evidence

ORD record
ord-dc8dd5d40e09446786402fc89e89795b
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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