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Lithium Hydroxide → 2-{[2-(4-{2-[(4-Chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoic acid

HRID 898903
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 898903
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][N:7]([CH2:31][CH3:32])[C:8](=[O:30])[CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][S:19][C:20]3[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=3[C:22]([O:24]C)=[O:23])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[Li+]>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:31][CH3:32])[C:8](=[O:30])[CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][S:19][C:20]3[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=3[C:22]([OH:24])=[O:23])=[CH:13][CH:12]=2)=[CH:33][CH:34]=1
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Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 69258846Methyl 2-{[2-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoate

Produkt 1

HCID 103230552-{[2-(4-{2-[(4-Chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoic acidAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

Methyl 2-{[2-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-ethyl]thio}benzoate (0.085 g, 0.170 mmol) was dissolved in a mixture of acetonitrile/water (1/1, 4 ml) and lithium hydroxide (0.008 g, 0.341 mmol) was added. The reaction was performed in an single node microwave oven (5 min. 150 deg). The solvent was removed by evaporation and then HCl (2 ml, 1 M) was added. The water phase was extracted with two portions of EtOAc (20 ml). The combined organic phase was dried (MgSO4) and the solvent was removed by evaporation and gave 0.073 g of 2-{[2-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoic acid (yield 88.4%) as an oil which solidified on cooling and standing.

Aufarbeitung

  1. additionwas added
  2. customThe reaction was performed in an single node microwave oven
  3. custom(5 min. 150 deg)
  4. customThe solvent was removed by evaporation
  5. additionHCl (2 ml, 1 M) was added
  6. extractionThe water phase was extracted with two portions of EtOAc (20 ml)
  7. dry with materialThe combined organic phase was dried (MgSO4)
  8. customthe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-3b4216d8d1f64001aa7ae2d34988d7b8
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07351858B2

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