Ethyl Acetate → HCID 22101898, compound

HRID 1458301Notes

Reaction equation

HRID 1458301 reaction equation
[CH2:1]([N:3]1[CH2:7][CH:6]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17]/[CH:18]=[C:19](/[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])\[CH3:20])=[CH:12][CH:11]=2)[CH2:5][N:4]1[CH2:28][CH3:29])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[CH2:7][CH:6]([NH:8][C:9](=[S:39])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17]/[CH:18]=[C:19](/[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])\[CH3:20])=[CH:12][CH:11]=2)[CH2:5][N:4]1[CH2:28][CH3:29])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 9908920HCID 9908920, compound

Product 1

HCID 22101898HCID 22101898, compoundYield 139.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-(1,2-diethyl-4-pyrazolidinyl)-4-geranyloxybenzamide (1.50 g) in toluene (50 ml) was added Lawesson's reagent (0.76 g). After the reaction solution was refluxed with heating for 30 minutes, ethyl acetate was added thereto. Then, the reaction solution was washed with aqueous sodium bicarbonate solution and then with brine. Its organic layer was concentrated under a vacuum and thus obtained residue was pulled by silica gel column chromatography (chloroform:methanol=30:1), thereby yielding 1.09 g (70%) of the aimed compound.

Workup

  1. temperatureAfter the reaction solution was refluxed
  2. temperaturewith heating for 30 minutes
  3. washThen, the reaction solution was washed with aqueous sodium bicarbonate solution
  4. concentrationIts organic layer was concentrated under a vacuum and thus obtained residue

Sources & evidence

ORD record
ord-6cc1e6f157c44da3a5f6ba11aa749b8c
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

Loading…