Pyridine → Methyl 2-(1-t-butoxycarbonyl-1-phenylthiomethylene)-1,3-dithietane-4-carboxylate

HRID 371122Notes

Reaction equation

HRID 371122 reaction equation
[C:1]([O:5][C:6]([CH:8]=[C:9]1[S:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[S:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:23]1([S:29]Cl)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:1]([O:5][C:6]([C:8](=[C:9]1[S:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[S:10]1)[S:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11008040Benzenesulfenyl chlorideHCID 20274244Methyl 2-(t-butoxycarbonylmethylene)-1,3-dithietane-4-carboxylate

Product 1

HCID 20274259Methyl 2-(1-t-butoxycarbonyl-1-phenylthiomethylene)-1,3-dithietane-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 2-(t-butoxycarbonylmethylene)-1,3-dithietane-4-carboxylate (689 mg), pyridine (430 μl) and benzenesulfenyl chloride is allowed to react in methylene chloride at 0° C. until no starting carboxylate is detected. The reaction mixture is washed with water, dried, and vacuum evaporated to give methyl 2-(1-t-butoxycarbonyl-1-phenylthiomethylene)-1,3-dithietane-4-carboxylate. Yield: 713 mg (73%).

Workup

  1. washThe reaction mixture is washed with water
  2. customdried
  3. customvacuum evaporated

Sources & evidence

ORD record
ord-65ee250340974e8aa798484f2e9d38eb
Source dataset
uspto-grants-1985_07
Patent number
US04529721

Reaction notes

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