Sodium Chloride → HCID 13174771, compound

HRID 2109360Notes

Reaction equation

HRID 2109360 reaction equation
[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:21]3[C:22](=[O:26])[C:23](Br)([Br:24])[C@H:20]3[S:19](=[O:27])[C:18]2([CH3:29])[CH3:28])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S([O-])([O-])(=O)=O.[Bi+3].S([O-])([O-])(=O)=O.S([O-])([O-])(=O)=O.[Bi+3].[Cl-].[Na+].[Mg]>ClCCl.O>[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:21]3[C:22](=[O:26])[CH2:23][C@H:20]3[S:19](=[O:27])[C:18]2([CH3:29])[CH3:28])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:21]3[C:22](=[O:26])[CH:23]([Br:24])[C@H:20]3[S:19](=[O:27])[C:18]2([CH3:29])[CH3:28])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 198144Bismuth(III) sulfateHCID 5462224MagnesiumHCID 14096412HCID 14096412, compound

Product 2

HCID 13174771HCID 13174771, compoundHCID 68995161HCID 68995161, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A 20 g quantity of Compound 1 was dissolved in 75 mL of dichloromethane. To the solution was added 0.9 g of bismuth sulfate and 30 mL of 20% aqueous solution of sodium chloride with stirring. To the mixture were added each of 0.5 to 0.6 g of magnesium ribbon at intervals of 30 minutes in total amount of 4 g. The mixture was stirred at room temperature for 10 hours. Water (100 mL) was added and an orgaic layer was separated. The organic layer was washed with 5% aqueous solution of sodium chloride. The organic layer was concentrated and the residue was subjected to column chromatography (toluene:ethyl acetate=5:1) to give Compound 2 and Compound 3, respectively.

Workup

  1. stirringThe mixture was stirred at room temperature for 10 hours
  2. customan orgaic layer was separated
  3. washThe organic layer was washed with 5% aqueous solution of sodium chloride
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-6946453f3ce049cda760473cbd1f54f9
Source dataset
uspto-grants-2009_04
Patent number
US07514553B2

Reaction notes

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