Sodium Carbonate → HCID 86739200, compound

HRID 2296353Notes

Reaction equation

HRID 2296353 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1SCCCS1)=[O:5])[CH3:2].ClN1[C:17](=O)[CH2:16][CH2:15][C:14]1=O.S([O-])([O-])=[O:21].[Na+].[Na+].[C:26](=[O:29])([O-])[O-].[Na+].[Na+].[CH3:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].ClCCl>C(#N)C.C(#N)C.O.[Cl-].[Na+].O.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([O:3][C:4](=[O:5])[C:6](=[O:21])[CH2:14][CH2:15][CH2:16][CH:17]1[C:35]2[CH:36]=[CH:37][CH:32]=[CH:33][C:34]=2[CH2:26][O:29]1)[CH3:2]

Participants

10

Reactant 5

HCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 31398ChlorosuccinimideHCID 88552Ethyl 1,3-dithiane-2-carboxylateHCID 21226440Methylenechloride Hexane

Product 1

HCID 86739200HCID 86739200, compound

Reagents, catalysts & solvents 4

HCID 24470Silver NitrateCatalystHCID 6342AcetonitrileSolventHCID 18373917Acetonitrile--water (1/1)SolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-[2,3-Dihydro-2-benzofuranyl)propyl]-1,3-dithiane-2-carboxylic acid ethyl ester (8.0 g) dissolved in acetonitrile (15 mls) was added rapidly to a stirred solution of N-chlorosuccinimide (120 g) and silver nitrate (17.6 g) in 80% acetonitrile-water at 25° C. After 10 minutes saturated solutions of sodium sulphite (50 mls), sodium carbonate (50 mls) and brine were added successively at one minute intervals. To this mixture, a solution of hexane-dichloromethane (1:1, 250 mls) was added followed by filtration through celite. The organic phase of the filtrate was separated and dried over anhydrous magnesium sulphate. Removal of the solvent gave an oil (5.0 g). The unstable product was used immediately in the next stage. M/e M+ 262.

Workup

  1. filtrationfollowed by filtration through celite
  2. customThe organic phase of the filtrate was separated
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-e3179a8f35014cd692eac7c473769305
Source dataset
uspto-grants-1984_01
Patent number
US04428940

Reaction notes

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