Dimethyl Disulfide → HCID 59424691, compound

HRID 1711003Notes

Reaction equation

HRID 1711003 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[Li]CCCC.[CH3:16][S:17]SC>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([S:17][CH3:16])[S:10][C:3]=12

Participants

5

Reactant 3

HCID 12232Dimethyl DisulfideHCID 112752517-Chlorothieno[3,2-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 59424691HCID 59424691, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2 (200 mg, 1.18 mmol) in dry THF (11 ml) at −78° C. was added n-BuLi (0.57 mL, 2.5M solution on hexane, 1.41 mmol) and the resultant brown precipitate was stirred for 10 minutes. Methyl disulfide (0.16 ml, 1.77 mmol) was added slowly, the mixture was stirred at −78° C. for 3 hours and partitioned between DCM and water. Organic phase was separated, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford title compound 229 (0.240 g, 94% yield, crude) as a yellow solid. MS (m/z): 216.1 (100%), 218.1 (39%) (M+1).

Workup

  1. stirringthe mixture was stirred at −78° C. for 3 hours
  2. custompartitioned between DCM and water
  3. customOrganic phase was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b24dad43817c4a87bb8dd8604f7e8387
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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