6533b86efe1ef96bd12cb24c

RESEARCH PRODUCT

N,N-Dimethylformamide Diethyl Acetal

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(1; R1 = Et, R2 = Me) [1188-33-6] C7H17NO2 (MW 147.25) InChI = 1S/C7H17NO2/c1-5-9-7(8(3)4)10-6-2/h7H,5-6H2,1-4H3 InChIKey = BWKAYBPLDRWMCJ-UHFFFAOYSA-N (2; R1 = Me, R2 = Me) [4637-24-5] C5H13NO2 (MW 119.19) InChI = 1S/C5H13NO2/c1-6(2)5(7-3)8-4/h5H,1-4H3 InChIKey = ZSXGLVDWWRXATF-UHFFFAOYSA-N (3; R1 = PhCH2, R2 = Me) [2016-04-8] C17H21NO2 (MW 271.39) InChI = 1S/C17H21NO2/c1-18(2)17(19-13-15-9-5-3-6-10-15)20-14-16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3 InChIKey = JFIKHFNGAURIIB-UHFFFAOYSA-N (4; R1 = Et, R2 = Et) [22630-13-3] C9H21NO2 (MW 175.31) InChI = 1S/C9H21NO2/c1-5-10(6-2)9(11-7-3)12-8-4/h9H,5-8H2,1-4H3 InChIKey = AYZXEGOJMRKZCV-UHFFFAOYSA-N (mild and selective reagents for alkylation, formylation, and aminomethylenation1) Alternate Name: DMF diethyl acetal. Physical Data: (1) bp 134–136 °C/760 mmHg; pKb 6.2.5 (2) bp 102–104 °C/720 mmHg; pKb 6.25.5 (3) bp 138–140 °C/0.5 mmHg; pKb 6.2.5 (4) bp 57–58 °C/20 mmHg; pKb 6.4.5 Solubility: sol a variety of inert solvents. Form Supplied in: pure liquid. Preparative Methods: (1) a solution of sodium alkoxide (1 mol) and the secondary amine (1.1 mol) in 200–300 mL of the respective alcohol is refluxed as chloroform (39.5 g, 0.33 mol) is added. The mixture is refluxed for 2 h and the filtrate obtained is distilled in vacuo. For example, N,N-diethylformamide diethyl acetal is obtained in 32% yield.7 (2) A solution of N,N-dialkyl(chloromethylene)ammonium chloride (Vilsmeier reagent, 1 mol) in 640–500 mL of chloroform is stirred while sodium alkoxide (2.1 mol) in 1 L of the respective alcohol is added. After 1 h at 20 °C the sodium chloride is separated and the mixture is distilled in vacuo. For example, the yield of DMF dimethyl acetal is 55%.2 Handling, Storage, and Precautions: most of the known orthoamide derivatives are colorless, distillable liquids with an amine-like smell. If moisture and presence of acids and high temperature are avoided, most of the reagents can be stored almost indefinitely. No significant toxicity has been reported.