Triethylamine → HCID 53863259, compound

HRID 1089304Notes

Reaction equation

HRID 1089304 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[C:10]([O:14][C:15](=[O:28])[CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>C(#N)C>[C:10]([O:14][C:15](=[O:28])[CH2:16][CH2:17][N:18]([CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Cl:1])[CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 119062-Chlorobenzyl chloride2×HCID 10945622Di-tert-butyl 3,3'-Iminodipropionate

Product 1

HCID 53863259HCID 53863259, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

45.06 g (0.27 mol) of 2-chlorobenzylchloride and 51 g (0.19 mol) of di-tert-butyl-3,3'-iminodipropionate were dissolved in 350 ml of acetonitrile, mixed with 28.3 g (0.28 mol) of triethylamine and refluxed. After 5 hours, 8.85 g (0.06 mol) of 2-chlorobenzylchloride and 9.34 g (0.09 mol) of triethylamine were again added. After being refluxed for 15 hours, the reaction mixture was concentrated by evaporation. The residue was taken up in 300 ml of water, 100 ml of HCl 5n and 300 ml of ether. The acidic water phase was made basic with NaOH (20 percent) and extracted three times with 100 ml of ether. 67.7 g (91 percent) of the subtitle compound (noted above) was obtained from the ether phase. Data concerning the compound was:

Workup

  1. temperaturerefluxed
  2. temperatureAfter being refluxed for 15 hours
  3. concentrationthe reaction mixture was concentrated by evaporation
  4. extractionextracted three times with 100 ml of ether

Sources & evidence

ORD record
ord-37251d2df4ca49118c78c99ab61f7385
Source dataset
uspto-grants-1990_10
Patent number
US04965359

Reaction notes

Loading…