Water → HCID 53939659, compound

HRID 362340Notes

Reaction equation

HRID 362340 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[I:18])=O.B.CSC.O>O1CCCC1.ClCCl.O1CCCC1>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[I:18]

Participants

6

Reactant 3

HCID 962WaterHCID 12423031(Dimethyl sulfide)trihydroboronHCID 54531491HCID 54531491, compound

Product 1

HCID 53939659HCID 53939659, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a suspension of 1.39 g (3 mmol) of 2-iodo-N-(2-iodophenyl)benzeneacetamide in 30 ml of tetrahydrofuran-dichloromethane (1:1) is added 3.75 ml of 2.0 molar borane-dimethylsulfide in tetrahydrofuran. The solution is stirred 1 hr at room temperature and then refluxed for 16 hours. The mixture is cooled and water slowly added dropwise until gas evolution ceases. The volatiles are removed under vacuum and the aqueous residue made alkaline with 2N sodium hydroxide. The mixture is extracted with ether (50 ml) and the extract is washed with brine and dried (Na2SO4). The solution is filtered through a thin pad hydrous magnesium silicate and the filter pad is washed with ether and the filtrate evaporated. The residual solid is washed with isooctane to give 1.20 g of white solid. Recrystallization from diethylether/hexane gives white crystals.

Workup

  1. temperaturerefluxed for 16 hours
  2. temperatureThe mixture is cooled
  3. customThe volatiles are removed under vacuum
  4. extractionThe mixture is extracted with ether (50 ml)
  5. washthe extract is washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationThe solution is filtered through a thin pad hydrous magnesium silicate
  8. washthe filter pad is washed with ether
  9. customthe filtrate evaporated
  10. washThe residual solid is washed with isooctane

Sources & evidence

ORD record
ord-41ad2138c0324ba4a8280f206216a815
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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