Reaktionsgleichung
[N:1]([CH2:4][CH2:5][NH:6][C:7](=[O:21])[CH2:8]CCCCCCCCCCCC)=[N+:2]=[N-:3].[C:22]1([S:28]CC(Cl)=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N(CCN)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[N:1]([CH2:4][CH2:5][NH:6][C:7](=[O:21])[CH2:8][S:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[N+:2]=[N-:3]Komponenten
6
Versuchsvorschrift
As in the synthesis of N-(2-azidoethyl)tetradecanamide, 2-(phenylthio)acetyl chloride (0.222 g, 1.19 mmol) was reacted with 2-azidoethanamine (0.102 g, 1.19 mmol) and triethylamine (0.240 g, 2.37 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-2-(phenylthio)acetamide (0.179 g, 64%). 1H NMR (300 MHz, CDCl3) δ 7.29 (m, 4H), δ 7.18 (m, 2H), δ 3.60 (s, 2H), 3.34 (m, 4H) ppm; 13C NMR (75 MHz, CDCl3) δ 168.6, 134.8, 129.5, 128.6, 127.1, 50.8, 39.3, 37.7 ppm; HRMS (ESI) calcd for C10H12N4OS (M+) 236.0732, found 236.0729.
Quellen und Nachweise
- ORD-Eintrag
- ord-38540c23f33f48509977ee22b86c60ba
- Quelldatensatz
- uspto-grants-2013_02
- Patentnummer
- US08367713B2
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