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Benzyl Bromide → Benzyl 5-{1-ethoxycarbonyl-1-[2-(3-phenylureido)thiazol-4-yl]methylene}rhodanine-3-acetate

HRID 2107178
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2107178
[CH2:1]([O:3][C:4]([C:6](=[C:22]1[S:26][C:25](=[S:27])[N:24]([CH2:28][C:29]([OH:31])=[O:30])[C:23]1=[O:32])[C:7]1[N:8]=[C:9]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[S:10][CH:11]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.CN(C)P(=O)(N(C)C)N(C)C>O>[CH2:1]([O:3][C:4]([C:6](=[C:22]1[S:26][C:25](=[S:27])[N:24]([CH2:28][C:29]([O:31][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:30])[C:23]1=[O:32])[C:7]1[N:8]=[C:9]([NH:12][C:13]([NH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:14])[S:10][CH:11]=1)=[O:5])[CH3:2]
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Komponenten

6

Edukt 4

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 12679HexamethylphosphoramideHCID 541363965-{1-Ethoxycarbonyl-1-[2-(3-phenylureido)thiazol-4-yl]methylene}rhodanine acetic acid

Produkt 1

HCID 54015007Benzyl 5-{1-ethoxycarbonyl-1-[2-(3-phenylureido)thiazol-4-yl]methylene}rhodanine-3-acetate

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture comprising 1 g of 5-{1-ethoxycarbonyl-1-[2-(3-phenylureido)thiazol-4-yl]methylene}rhodanine-3-acetic acid, 0.25 g of triethylamine, 0.7 g of benzyl bromide and 10 ml of hexamethylphosphoric triamide was stirred at room temperature overnight. The reaction mixture was then poured into water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography, using as eluent a 2:1 by volume mixture of hexane and ethyl acetate. The resulting product was a yellow powder having the following physical properties.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. additionby volume mixture of hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f73dea69841440f1b3e63f93a615af11
Quelldatensatz
uspto-grants-1990_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04933355

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