Hydrogen Peroxide → HCID 14627775, compound

HRID 1109554Notes

Reaction equation

HRID 1109554 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>[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

5

Reactant 3

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

Product 1

HCID 14627775HCID 14627775, compound

Reagents, catalysts & solvents 1

HCID 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 nBu4.NHSO4 (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. additiontreated with the phase-transfer catalyst nBu4
  3. customAfter dilution with dichloromethane the layers were separated
  4. washthe organic phase washed with water and with dil. aq. NaHSO3
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-692988fe481e4f16ae50f5611e655e19
Source dataset
uspto-grants-1994_06
Patent number
US05321047

Reaction notes

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