Tetrahydrofuran → HCID 59215205, compound

HRID 1173744Notes

Reaction equation

HRID 1173744 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9]([CH2:19]C(C)C)=[C:10]([S:15]([O-])(=O)=O)C=CC=2C)=[CH:4][CH:3]=1.[CH2:23]1COCC1>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([CH3:19])[CH2:10][S:15][CH3:23])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 131727985HCID 131727985, compound

Product 1

HCID 59215205HCID 59215205, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
55 °C

Procedure

A solution 3-(6-chloropyridin-3-yl)-2-methylpropyl-4-methyl-benzenesulfonate (5.0 g, 14.7 mmol) and sodium methylthiolate (2.10 g, 30 mmol) in THF (50 mL) was stirred overnight at room temperature. The remaining unreacted starting material indicated on TLC was converted into the product completely after the solution was heated at 55° C. for 4 more hours. The mixture was diluted with ether and washed with 2 N NaOH solution (50 mL). The aqueous phase was washed with ether (50 mL). The combined organic phase was washed with brine (50 mL), dried over MgSO4, filtered and concentrated to give 2.94 g of the desired crude sulfide in 93% yield as a yellowish oil: M+=215, 217; δ 2.07 (s, 3H), 0.95 (d, 3H).

Workup

  1. washwashed with 2 N NaOH solution (50 mL)
  2. washThe aqueous phase was washed with ether (50 mL)
  3. washThe combined organic phase was washed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-05536e347eff4dfcb193967e97804888
Source dataset
uspto-grants-2010_11
Patent number
US07834188B2

Reaction notes

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