Diethylaminoethyl chloride

Cationic Starches. The two general categories of commercial cationic starches are tertiary and quaternary aminoalkyl ethers. Tertiary aminoalkyl ethers are prepared by treating an alkaline starch dispersion with a tertiary amine containing a P-halogenated alkyl, 3-chloto-2-hydtoxyptopyl radical, or a 2,3-epoxypropyl group. Under these reaction conditions, starch ethers are formed that contain tertiary amine free bases. Treatment with acid easily produces the cationic form. Amines used in this reaction include 2-dimethylaminoethyl chloride, 2-diethylaminoethyl chloride, and A/-(2,3-epoxypropyl) diethylamine. Commercial preparation of low DS derivatives employ reaction times of 6—12 h at 40—45°C for complete reaction. The final product is filtered, washed, and dried. 

The antifungal agent, dianithazole (76), is prepared by cleaving the ether function of 2-dimethylamino-6-ethoxybenzothia-zole (74) with aluminum chloride in chlorobenzene and then alkylating the sodium salt of the resulting phenol (75) with 2-diethylaminoethyl chloride. 

Diethylaminoethyl chloride Cyciopentyl (a-thienyIIhydroxyacetic acid Methyl bromide... 

N-Benzoyl-DL-tyrosil-di-n-propylamide Sodium methylate 2-Diethylaminoethyl chloride... 

Phenyl-(a-thienyl)hydroxyacetic acid (4.86 g), 2-diethylaminoethyl chloride (2.85 g) and 75 ml of isopropyl alcohol were refluxed for 15 h. After the addition of 50 ml of absolute alcohol to the cold mixture, it was treated with Norite (activated charcoal) at room temperature, filtered, and the solvents removed under reduced pressure. The residue crystallised when triturated with absolute ether. After recrystallisation from absolute alcohol, the phenyl-(a-thienyl)hydroxyacetate of 2-diethylaminoethyl hydrochloride melted at 181-182°C. 

Table 7 Relative Distribution of 2-Diethylaminoethyl (DEAE) Groups from Treating Methyl p-o-Glucopyranoside and Five Cellulose Samples with 2-Diethylaminoethyl Chloride in 0.5 M NaOH at 25°C for 45 min...

Diethylaminoethyl chloride hydrochloride Diethyl diazomalonate DiethyUndoloindole DiethyUsopropylsilyl... 

To 3(X) g. (1.75 moles) of the brown product above are added 100 g. of finely crushed ice and 400 ml. of ether. A cold solution of 70 g. (1.75 moles) of sodium hydroxide in 150 ml. of water is added with stirring, the temperature of the reaction mixture being held at 5° during this operation. After standing several minutes, the ether layer is separated and dried over Drierite. Removal of the ether under vacuum gives 202 g. (85% yield based on the hydrochloride) of 2-diethylaminoethyl chloride (Caution—toxic material) as a red oil. Further purification may be effected by distillation, the product boiling at 69°/50 mm. The free base is unstable and should be made up as needed from the stable hydrochloride salt. 

CeHiaS, Hexamethylene mercaptan.. . 172 CeHiaClN, 2-Diethylaminoethyl chloride. 116... 

Preparation of cationic starches, done with reagents such as 2-diethylaminoethyl chloride, 2,3-epoxypropyldiethylamine, or by cross-linking starch with epichlorohydrin in the presence of ammonia. The reaction with 2-diethylaminoethyl chloride is done at pH 11 to 12, followed by neutralization with acids. 

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