Hydrogen Peroxide → HCID 54280630, compound

HRID 861402Notes

Reaction equation

HRID 861402 reaction equation
[C:1]1([C:7]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH2:9][CH2:10][C:11]#[N:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:20]O.[OH-].[Na+].O>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]1([C:7]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:8][CH2:9][CH2:10][C:11]([NH2:12])=[O:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 54493883HCID 54493883, compound

Product 1

HCID 54280630HCID 54280630, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

5,6-Diphenyl-4-hexenenitrile (36 g) was dissolved in methylene chloride (180 mL) at 0° C. and stirred vigorously while 50% H2O2 (100 mL), tetrabutyl ammonium hydrogen sulfate (13 g) and 20% NaOH (100 mL) were added successively. The resulting mixture was stirred at 0° C. for 30 minutes, then for 2 hours without cooling. The reaction mixture was poured into CH2Cl2 and water and the organic layer was separated, washed with water and brine and dried (MgSO4). Concentration of the solvent afforded the crude amide which was purified by silica gel chromatography and elution with 50% ethyl acetate: hexane, then ethyl acetate to give the amide as a solid (30 g).

Workup

  1. additionwere added successively
  2. temperaturefor 2 hours without cooling
  3. customthe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. customConcentration of the solvent afforded the crude amide which
  7. customwas purified by silica gel chromatography and elution with 50% ethyl acetate

Sources & evidence

ORD record
ord-d98e57bcbdb64c7ca2a66e691f14f71f
Source dataset
uspto-grants-1998_02
Patent number
US05714500

Reaction notes

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