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Chlorine → Methyl 2-(1-t-butoxycarbonyl-1-difluoromethylthiomethylene)-1,3-dithietane-4-carboxylate

HRID 371123
Notes
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Reaction equation

HRID 371123 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].[F:17][CH:18]([F:21])[S:19]Cl.C(SC(F)F)C1C=CC=CC=1.ClCl>ClCCl.N1C=CC=CC=1>[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:19][CH:18]([F:21])[F:17])=[O:7])([CH3:3])([CH3:4])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24526ChlorineHCID 11557371(((Difluoromethyl)sulfanyl)methyl)benzeneHCID 20274244Methyl 2-(t-butoxycarbonylmethylene)-1,3-dithietane-4-carboxylateHCID 22618524(Chlorosulfanyl)(difluoro)methane

Product 1

HCID 86740197Methyl 2-(1-t-butoxycarbonyl-1-difluoromethylthiomethylene)-1,3-dithietane-4-carboxylate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(t-butoxycarbonylmethylene)-1,3-dithietane-4-carboxylate (1.05 g) is reacted with difluoromethylsulphenyl chloride, which was synthesized from difluoromethyl benzyl thioether (1.74 g) and chlorine, in dichloromethane (5 ml) at room temperature in the presence of pyridine (0.65 ml) until no starting carboxylate is detected in the reaction mixture. The mixture is then washed with a 5% sodium thiosulfate solution and 10% HCl, dried, and concentrated in vacuo to give methyl 2-(1-t-butoxycarbonyl-1-difluoromethylthiomethylene)-1,3-dithietane-4-carboxylate.

Workup

  1. washThe mixture is then washed with a 5% sodium thiosulfate solution and 10% HCl
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31a07c12f9844761944a56a0f0e8587e
Source dataset
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04529721

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes