Dimethylformamide → HCID 21401043, compound

HRID 973141Notes

Reaction equation

HRID 973141 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][C:6](=[C:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[NH:11][C:10]([CH3:17])([CH3:16])[CH2:9]2)[CH2:5][C:4]([CH3:19])([CH3:18])[NH:3]1.C(N([CH2:26][CH3:27])CC)C.[C:28](Cl)(=[O:31])[CH:29]=[CH2:30].CN(C)[CH:35]=[O:36]>>[C:28]([N:11]1[C:10]([CH3:17])([CH3:16])[CH2:9][C:8](=[C:6]2[CH2:5][C:4]([CH3:19])([CH3:18])[N:3]([C:35](=[O:36])[CH:26]=[CH2:27])[C:2]([CH3:20])([CH3:1])[CH2:7]2)[CH2:13][C:12]1([CH3:15])[CH3:14])(=[O:31])[CH:29]=[CH2:30]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 21401015HCID 21401015, compound

Product 1

HCID 21401043HCID 21401043, compound

Procedure

A mixture of 5.6 g of 2,2,2',2',6,6,6',6'-octamethyl-4,4'-bipiperidylidene, 5.0 g of triethylamine and 50 ml of dimethylformamide was cooled to 5°-10° C, and 4.5 g of acrylyl chloride was added dropwise thereto. After completion of the addition, the mixture was stirred at room temperature for one hour and then at 105°-110° C for 3 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the resulting residue was extracted with benzene. The extract was washed with 10% aqueous sodium carbonate solution and dried over potassium carbonate. The residue was purified by column chromatography on silica gel (eluted with a 10:1 mixture of benene and ethyl acetate), then by recrystallization from a 5:1 mixture of isopropyl ether and benzene, to give 1.2 g of the desired product melting at 196°-198° C.

Workup

  1. temperaturewas cooled to 5°-10° C
  2. additionAfter completion of the addition
  3. waitat 105°-110° C for 3 hours
  4. customAfter completion of the reaction
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. extractionthe resulting residue was extracted with benzene
  7. washThe extract was washed with 10% aqueous sodium carbonate solution
  8. dry with materialdried over potassium carbonate
  9. customThe residue was purified by column chromatography on silica gel (
  10. washeluted with a 10:1 mixture of benene and ethyl acetate), then
  11. customby recrystallization
  12. additionfrom a 5:1 mixture of isopropyl ether and benzene

Sources & evidence

ORD record
ord-8b7360c67ec649d7834501e6289aefe2
Source dataset
uspto-grants-1977_10
Patent number
US04055536

Reaction notes

Loading…