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- W2131716715 abstract "[20353-93-9] C6H14ClN3 (MW 163.65) InChI = 1S/C6H14N3.ClH/c1-8(2)5-7-6-9(3)4;/h5-6H,1-4H3;1H/q+1;/p-1 InChIKey = DEIBXAPEZDJDRC-UHFFFAOYSA-M (β-dimethylaminomethylenating agent for ketones and amines;2 yields enamino derivatives of esters and lactones;3 converts Grignard reagents to aldehydes4) Alternate Name: Gold's reagent. Physical Data: mp 100–102 °C. Solubility: sol water, chloroform; insol nonpolar organic solvents. Form Supplied in: tan to dark brown solid; commercially available. Preparative Methods: 5 a 1 L, one-necked, round-bottomed flask is equipped with a Claisen adapter, mechanical stirrer, reflux condenser, and mineral oil bubbler. The flask is charged with cyanuric chloride (73.8 g, 0.4 mol) (Caution: cyanuric chloride is a lachrymator and causes burns on contact with the skin), N,N‐Dimethylformamide (175.4 g, 2.4 mol) and 1,4-dioxane (100 mL). The resulting solution is stirred and heated at 85 °C for 2–3 h while a considerable amount of carbon dioxide is evolved. When gas evolution is minimal, the reaction mixture is allowed to cool to room temperature; the product rapidly solidifies (eq 1). The flask which contains the solid product is connected to an isopropyl alcohol/dry ice trap and the solvent is removed by evacuating the system to approximately 0.05 mmHg. The crude product weighs 186–187 g (95% yield). Another method of isolating the product is by rapid filtration and washing with acetone. (1) Analysis of Reagent Purity: 1H NMR (CDCl3) δ 3.27 (s, 6H, two CH3), 3.43 (s, 6H, two CH3), 9.57 (s, 2H, CHN). Handling, Storage, and Precautions: Gold's reagent is very hygroscopic and should be handled under a moisture-free environment. If kept dry, it has a substantial shelf-life. Store in desiccator over anhydrous calcium sulfate." @default.
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- W2131716715 date "2001-04-15" @default.
- W2131716715 modified "2023-09-26" @default.
- W2131716715 title "[[[(Dimethylamino)methylene]amino]methylene]dimethylammonium Chloride" @default.
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- W2131716715 doi "https://doi.org/10.1002/047084289x.rd304m" @default.
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