Hydrogen Peroxide → HCID 14627775, compound

HRID 260599Notes

Reaction equation

HRID 260599 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]([CH2:16][CH2:17][CH2:18][C:19]#[N:20])[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-:23].[Na+].OO>ClCCl.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:16][CH2:17][CH2:18][C:19]([NH2:20])=[O:23])[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 14627771HCID 14627771, compound

Product 1

HCID 14627775HCID 14627775, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[N,N-Bis-(4-chlorobenzyl)amino]butyronitrile (2.0 g) prepared according to Example 1 in dichloromethane (10 ml) was cooled in ice, then treated with the phase-transfer catalyst nBu4NHSO4 (0.5 g), 20% aq NaOH (3.2 ml ) and 30% H2O2 (4.0 ml ). The mixture was stirred vigorously at 0° for about half an hour, then at room temperature for 23 hours. After dilution with dichloromethane the layers were separated, and the organic phase washed with water and with dil. aq. NaHSO3, then dried (MgSO4) Filtration and evaporation gave a syrup (2.26 g) which was flash-chromatographed on neutral alumina eluted with neat toluene (to remove starting material (0.3 g )) and then with 10% EtOH-toluene to recover the product (1.62 g). Repeat chromatography on silica eluted with 2-5% EtOH-toluene gave the title compound (1.55 g; 73.6%) as a syrup which set solid on standing. The resulting crystals had m.p. 66°-76°.

Workup

  1. temperaturewas cooled in ice
  2. customAfter dilution with dichloromethane the layers were separated
  3. washthe organic phase washed with water and with dil. aq. NaHSO3
  4. customdried
  5. filtration(MgSO4) Filtration and evaporation

Sources & evidence

ORD record
ord-4f3c49e4521d4eb1acc9ade9310725c0
Source dataset
uspto-grants-1996_06
Patent number
US05527955

Reaction notes

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