Triethylamine → HCID 53863259, compound

HRID 981322Notes

Reaction equation

HRID 981322 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 in 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. additionin added
  3. temperatureAfter being refluxed for 15 hours
  4. concentrationthe reaction mixture was concentrated by evaporation
  5. extractionextracted three times with 100 ml of ether

Sources & evidence

ORD record
ord-e9b10b1657fa4a0989affb4765c6b831
Source dataset
uspto-grants-1991_02
Patent number
US04990618

Reaction notes

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