Dimethyl Disulfide → HCID 10831033, compound

HRID 2292759Notes

Reaction equation

HRID 2292759 reaction equation
S(Cl)(Cl)(=O)=O.CS[S:8][CH3:9].[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:16]=[C:15]2[CH2:28][C:29]([NH2:31])=[O:30].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]([S:8][CH3:9])=[C:15]2[CH2:28][C:29]([NH2:31])=[O:30]

Participants

6

Reactant 4

HCID 12232Dimethyl DisulfideHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 10732550HCID 10732550, compound

Product 1

HCID 10831033HCID 10831033, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sulfuryl chloride (0.8 mL, 10 mmol) was added to an ice-bath cooled solution of 1.0 mL of dimethyldisulfide in 25 mL of methylene chloride, the cooling bath removed, and the mixture allowed to warm to room temperature. Three mL of this solution (containing methanesulfenyl chloride) was added to 320 mg (1.1 mmol) of 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide (Example 3) in 100 mL of methylene chloride, stirred 0.33 hours, saturated NaHCO3 solution added, stirred well, and the methylene chloride solution separated, washed with saturated NaCl, dried (Na2SO4), and concentrated at reduced pressure. The residue chromatographed on silica was eluted with 40% EtOAc/hexane→100% EtOAc to give 115 mg (31% yield) of 5-methoxy-2-(methylthio)-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 195°-197° C.

Workup

  1. customthe cooling bath removed
  2. stirringstirred well
  3. customthe methylene chloride solution separated
  4. washwashed with saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated at reduced pressure
  7. customThe residue chromatographed on silica
  8. washwas eluted with 40% EtOAc/hexane→100% EtOAc

Sources & evidence

ORD record
ord-b629d07ae74644c1b008fbe13f2bc892
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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