Tetrahydrofuran → HCID 86620020, compound

HRID 2234213Notes

Reaction equation

HRID 2234213 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-d8c34f8572484e33a53b1e6016e15171
Source dataset
uspto-grants-2010_05
Patent number
US07709649B2

Reaction notes

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