Water → HCID 53798517, compound

HRID 256381

Reaction equation

HRID 256381 reaction equation
ClN1[C:6](=O)[CH2:5][CH2:4][C:3]1=[O:8].[C:9]1([Se][Se]C2C=CC=CC=2)[CH:14]=CC=C[CH:10]=1.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.[K].O>CN(C=O)C>[O:8]1[CH:3]=[CH:4][CH:5]=[C:6]1[C:9]([CH3:14])=[CH:10][N:27]1[C:23](=[O:33])[C:24]2=[CH:32][CH:31]=[CH:30][CH:29]=[C:25]2[C:26]1=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 15460Diphenyl diselenideHCID 31398ChlorosuccinimideHCID 24194345Phthalimide potassium salt

Product 1

HCID 53798517HCID 53798517, compoundYield 299.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 8.35 g (0.077 mole) of the olefin of Step A in 310 ml of DMF was added 12.37 g (0.093 mole) of N-chlorosuccinimide and 1.46 g (0.0047 mole) of diphenyl diselenide. After 3 hours at room temperature the mixture was partitioned between 500 ml of hexane and 1000 ml of 5% Na2S2O3. The hexane was distilled off at atmospheric pressure and the residue was dissolved in 200 ml of DMF, 9.49 g (0.051 mole) of potassium phthalimide was added and the mixture was warmed to 90° C. under N2. After 45 min. the cooled reaction mixture was poured into water and the precipitated product was filtered off and recrystallized from ethylacetate/2-propanol, affording 3.57 g colorless crystals, mp. 136°-137° C.

Workup

  1. customAfter 3 hours at room temperature the mixture was partitioned between 500 ml of hexane and 1000 ml of 5% Na2S2O3
  2. distillationThe hexane was distilled off at atmospheric pressure
  3. dissolutionthe residue was dissolved in 200 ml of DMF
  4. customAfter 45 min. the cooled reaction mixture
  5. filtrationthe precipitated product was filtered off
  6. customrecrystallized from ethylacetate/2-propanol

Sources & evidence

ORD record
ord-7c326113c7934c3eaca585bb14d50dfc
Source dataset
uspto-grants-1987_10
Patent number
US04703058

Linked notes

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