2-CHLORO-N-PROP-2-YNYLACETAMIDE synthesis
- Product Name:2-CHLORO-N-PROP-2-YNYLACETAMIDE
- CAS Number:7458-03-9
- Molecular formula:C5H6ClNO
- Molecular Weight:131.56
Yield:7458-03-9 99%
Reaction Conditions:
with triethylamine in dichloromethane at 0 - 20; for 3 h;Huisgen Cycloaddition;
Steps:
3.2.1. Synthesis of N-Prop-2-ynylamide (8a-8o)
General procedure: The compounds 8a-8o were all synthesized by the following general procedure. To a solutioncontaining 7a (5 g, 40.94 mmol) and DMF (0.05 mL, 0.65 mmol) dissolved in dichloromethane (100 mL)was added a solution of oxalyl chloride (3.8 mL, 45.03 mmol) dissolved in dichloromethane (10 mL)dropwise at 0 °C. After stirring the reaction mixture at r.t. for 3 h, the solution was concentrated underreduced pressure to give the corresponding acyl chloride. To a solution composed of propargylamine(3.1 mL, 45.03 mmol) and triethylamine (8.5 mL, 61.41 mmol) dissolved in dichloromethane (100 mL)was added dropwise at 0 ° C a solution of the corresponding acyl chloride previously dissolved indichloromethane (30 mL). After stirring at r.t. for 3 h, the mixture was washed with a solution ofdiluted hydrochloric acid (1 M, 100 mL) followed by an extraction with dichloromethane (3 100 mL).The combined organic layers were then dried over anhydrous sodium sulfate and then concentratedunder reduced pressure to afford the crude product 8a. The residue was then crystallized with amixture of ethyl acetate/petroleum ether to afford the pure product 8a. The spectral data for thecompounds 8a-8o are given in the Supporting-Information.
References:
Tian, Hao;Xu, Yiren;Liu, Shaojin;Jin, Dingsha;Zhang, Jianjun;Duan, Liusheng;Tan, Weiming [Molecules,2017,vol. 22,# 5,art. no. 694] Location in patent:supporting information
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