Tetrahydrofuran → HCID 86620020, compound

HRID 1924845Notes

Reaction equation

HRID 1924845 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=CC(CCl)=C[N:3]=1.[CH3:11][S-:12].[Na+].[CH2:14]1[CH2:18]O[CH2:16][CH2:15]1>CCOCC>[Cl:1][C:2]1[C:7]([Cl:8])=[C:14]([CH3:18])[C:15]([S:12][CH3:11])=[CH:16][N:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4378561Sodium methanethiolateHCID 101765362,3-Dichloro-5-(chloromethyl)pyridine

Product 1

HCID 86620020HCID 86620020, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2,3-dichloro-5-chloromethylpyridine (3.75 g, 19.1 mmol) in THF (30 mL) was added solid sodium thiomethoxide (2.01 g, 29 mmol) in one portion and the resulting mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with ether (100 mL), washed with 0.1 N aqueous HCl (50 mL) solution and brine (50 mL), dried over anhydrous MgSO4, filtered, concentrated, and dried to give 3.55 g of 2,3-dichloro-5-methylthio-methylpyridine as a dark yellow liquid in 89% crude yield. The crude product was analytically pure without further purification. GC-MS: calcd for C7H7Cl2NS [M]+ 208. Found 208.

Workup

  1. washwashed with 0.1 N aqueous HCl (50 mL) solution and brine (50 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customdried

Sources & evidence

ORD record
ord-399839be7f3543ed94d549e784ac508d
Source dataset
uspto-grants-2012_05
Patent number
US08178565B2

Reaction notes

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