Triethylamine → N-ethoxalyl-N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline

HRID 482053Notes

Reaction equation

[C:1]1(=[O:28])[N:5]([CH2:6][CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([F:22])([F:21])[CH:18]([F:20])[F:19])=[CH:11][CH:10]=2)[C:4](=[O:23])[C:3]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:2]12.C(N(CC)CC)C.Cl[C:37](=[O:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39]>ClCCl>[C:37]([N:8]([CH2:7][CH2:6][N:5]1[C:4](=[O:23])[C:3]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:2]2[C:1]1=[O:28])[C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]([F:22])([F:21])[CH:18]([F:19])[F:20])=[CH:13][CH:14]=1)([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:43]

Participants

Conditions

Temperature: -40 °C

Procedure

To the mixture of the obtained N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline (3.2 g), triethylamine (1.2 ml) and dichloromethane (60 ml), was added dropwise a solution of ethyl chloroglyoxylate (0.9 ml) in dichloromethane (10 ml) at -65° C. The reaction solution was stirred for 1 hour at -40° C., and then ice-water (50 ml) was added thereto to fractionate. The dichloromethane layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give N-ethoxalyl-N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline (3.1 g) as colorless powdery crystals.

Workup

washThe dichloromethane layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-5a0f0de434c74bf3920ee54530e32bac
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05792780

Reaction notes

Loading…