3-(1-trityl-1H-imidazol-4-yl)propan-1-amine → 1-[3-(1-triphenylmethylimidazol-4-yl)propyl]-3-[3-[N-(4-bromobenzyl)-N-(pyridin-2-yl)amino]propyl]thiourea

HRID 365282

Reaktionsgleichung

Reaktionsgleichung von HRID 365282
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]([CH2:14][CH2:15][CH2:16][N:17]=[C:18]=[S:19])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:22]1([C:28]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:29]2[CH:33]=[C:32]([CH2:34][CH2:35][CH2:36][NH2:37])[N:31]=[CH:30]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[C:44]1([C:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:29]2[CH:33]=[C:32]([CH2:34][CH2:35][CH2:36][NH:37][C:18]([NH:17][CH2:16][CH2:15][CH2:14][N:7]([CH2:6][C:5]3[CH:20]=[CH:21][C:2]([Br:1])=[CH:3][CH:4]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)=[S:19])[N:31]=[CH:30]2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Komponenten

4

Edukt 2

HCID 153458253-(1-trityl-1H-imidazol-4-yl)propan-1-amineHCID 22118507HCID 22118507, Verbindung

Produkt 1

HCID 221185151-[3-(1-triphenylmethylimidazol-4-yl)propyl]-3-[3-[N-(4-bromobenzyl)-N-(pyridin-2-yl)amino]propyl]thioureaAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

N-(4-bromobenzyl)-N-(3-isothiocyanatopropyl)-N-(pyridin-2-yl)amine(1 g, 2.76 mmol) and 3-(1-triphenylmethylimidazol-4-yl)propylamine (1.014 g, 2.76 mmol) were dissolved in chloroform (10 ml) and heated at reflux for 4 h. The solvent was removed by evaporation in vacuo and the residue (3.09 g) purified by column chromatography on silica gel (400 ml) using ethyl acetate/methanol/triethylamine 9:0.5:0.5 as eluent affording 1.59 g (80%) of pure 1-[3-(1-triphenylmethylimidazol-4-yl)propyl]-3-[3-[N-(4-bromobenzyl)-N-(pyridin-2-yl)amino]propyl]thiourea.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. customThe solvent was removed by evaporation in vacuo
  4. customthe residue (3.09 g) purified by column chromatography on silica gel (400 ml)

Quellen und Nachweise

ORD-Eintrag
ord-7db9d80f2df64dc6835abcda7aa64ffe
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127343

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