Bismuth trichloride → HCID 13174771, compound

HRID 2109356Notes

Reaction equation

HRID 2109356 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.[Cl-].[NH4+].[Bi](Cl)(Cl)Cl.[Al]>ClCCl.O.CO>[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 24591Bismuth trichlorideHCID 25517Ammonium ChlorideHCID 5359268AluminumHCID 14096412HCID 14096412, compound

Product 1

HCID 13174771HCID 13174771, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A 82.6 g quantity of Compound 1 was dissolved in 300 mL of dichloromethane. To the solution was added 115 mL of 20% aqueous solution of ammonium chloride and 36 mL of methanol with stirring. After adding 1.6 g of bismuth chloride, 10 g of aluminum powder was gradually added to the mixture while maintaining at 20 to 30° C. The mixture was reacted for 5 hours while maintaining at 20 to 30° C. After adding 120 mL of water, insoluble metalresidue was filtered and an orgaic layer was separated. The organic layer was washed with 120 mL of 5% aqueous solution of sodium chloride. The organic layer was concentrated to give Compound 2.

Workup

  1. additionwas gradually added to the mixture
  2. customThe mixture was reacted for 5 hours
  3. temperaturewhile maintaining at 20 to 30° C
  4. filtrationwas filtered
  5. customan orgaic layer was separated
  6. washThe organic layer was washed with 120 mL of 5% aqueous solution of sodium chloride
  7. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-cdb25f240c05443da02dd453a9c6874c
Source dataset
uspto-grants-2009_04
Patent number
US07514553B2

Reaction notes

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