Methanol → HCID 13174771, compound

HRID 2109359Notes

Reaction equation

HRID 2109359 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)[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+].CO>ClCCl.[Fe].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

Participants

8

Reactant 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 198144Bismuth(III) sulfate2×HCID 14096412HCID 14096412, compound

Product 1

HCID 13174771HCID 13174771, compoundYield 89.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A 42 g quantity of Compound 1 was dissolved in 300 mL of dichloromethane. To the solution was added 0.9 g of bismuth sulfate and 57 mL of 20% aqueous solution of sodium chloride with stirring. To the mixture were added 10 g of iron powder and 17 mL of methanol with stirring at room temperature for 9 hours. Further, the mixture was stirred for 10 hours with adding 0.8 g of bismuth sulfate, and stirred at 35° C. for 2 hours. After completion of reaction, 100 mL of water was added and an orgaic layer was separated. The organic layer was washed with 100 mL of 5% aqueous solution of sodium chloride. The organic layer was concentrated to give Compound 2.

Workup

  1. stirringwith stirring at room temperature for 9 hours
  2. stirringFurther, the mixture was stirred for 10 hours
  3. stirringstirred at 35° C. for 2 hours
  4. additionwas added
  5. customan orgaic layer was separated
  6. washThe organic layer was washed with 100 mL of 5% aqueous solution of sodium chloride
  7. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-53ffe91fdb3146918efccde0649e3ed3
Source dataset
uspto-grants-2009_04
Patent number
US07514553B2

Reaction notes

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