Acetonitrile → Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) Azodicarboxylate

HRID 742615Notes

Reaction equation

HRID 742615 reaction equation
[NH:1]([C:17]([O:19][CH:20]1[CH2:25][C:24]([CH3:27])([CH3:26])[N:23]([CH3:28])[C:22]([CH3:30])([CH3:29])[CH2:21]1)=[O:18])[NH:2][C:3]([O:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([CH3:14])[C:8]([CH3:16])([CH3:15])[CH2:7]1)=[O:4].FC(F)(F)C(O)=O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C(#N)C>C(Cl)Cl>[N:2]([C:3]([O:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([CH3:14])[C:8]([CH3:16])([CH3:15])[CH2:7]1)=[O:4])=[N:1][C:17]([O:19][CH:20]1[CH2:21][C:22]([CH3:29])([CH3:30])[N:23]([CH3:28])[C:24]([CH3:27])([CH3:26])[CH2:25]1)=[O:18]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 12217721Iodo benzene diacetateHCID 53819262Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) Hydrazine-1,2-dicarboxylate

Product 1

HCID 54508599Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) AzodicarboxylateYield 23.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 30.0 g bis(1,2,2,6,6-pentamethylpiperidin-4-yl) hydrazine-1,2-dicarboxylate in 60 mL of methylene chloride is added 16.0 g (10.8 mL), of trifiuoroacetic acid at 0°-5° C., followed the addition of 22.6 g of iodobenzene diacetate at room temperature. After stirring at room temperature for 2.5 hours, the reaction mixture is washed with saturated sodium bicarbonate solution and then with brine, and dried over anhydrous magnesium sulfate. The dried solution is evaporated to afford a pale yellow oil. Trituration with acetonitrile affords 7.0 g of the title compound as a pale yellow solid; mp 135°-137° C. NMR and IR analyses are consistent with the desired structure.

Workup

  1. customat 0°-5° C.
  2. washthe reaction mixture is washed with saturated sodium bicarbonate solution
  3. dry with materialwith brine, and dried over anhydrous magnesium sulfate
  4. customThe dried solution is evaporated
  5. customto afford a pale yellow oil

Sources & evidence

ORD record
ord-96d0c6c4aaf8479fadff1c0bc672f05d
Source dataset
uspto-grants-1996_09
Patent number
US05554754

Reaction notes

Loading…