Bromoethylamine hydrobromide

Starting from 2-bromoethylamine hydrobromide and selenourea, Chu and Mautner (60) prepared the salt of 2-(aminoethyl)-selenopseudourea, which cyclizes upon heating in aqueous solution to give 2-aminoselenazoline (Scheme 58). 

Amino-A.-selenazoline and its 5-methyl derivative have previously been obtained by Baringer (61) starting from 2-bromoethylamine hydrobromide and l-amino-2-bromopropane hydrobromide, respectively, by reaction with potassium selenocyanate. 

B-Chloro-N-methylanthranilic acid Bromoethylamine hydrobromide Calcium carbonate Sodium hydroxide Phosphorus oxychioride... 

A) Preparation of 4-Acetyl-7-Chloro-1,2,3,4-Tetrahydro-1-Methyl-5H-1,4-Bemodiazepin-5-one A mixture of 68.5 g (0.37 mol) of 5-chloro-N-methylanthranilic acid, 51 g (0.51 mol) of calcium carbonate, 76 g (0.37 mol) of bromoethylamine hydrobromide and 2.5 liters of water was stirred and heated under reflux for 3 hours. A solution of 23.4 g (0.26 mol) of anhydrous oxalic acid in 250 ml of water was slowly added to the refluxing mixture. The precipitated calcium oxalate was filtered off, and the filtrate adjusted to pH 7 with concentrated ammonium hydroxide. The filtrate was then concentrated to dryness in vacuo and the residue heated on the steam bath with 400 ml of 6 N ethanolic hydrogen chloride until the residue was crystalline. Filtration gave 122 g of N-(aminoethyl)-5-chloro-N-methylanthranilic acid hydrochloride as a solid. 

The dark-colored residue is divided into two approximately equal portions, and each is poured, while still hot, into a 4-I. beaker. After the liquid has cooled to about 70°, 1650 cc. of acetone is added to each portion. The mixture is stirred well, so that as much as possible of the dark-colored solid is brought into contact with the acetone. After standing in the ice box overnight, the jS-bromoethylamine hydrobromide is collected on a filter, washed with acetone until colorless (Note 3), and air-dried... 

Bromoethylamine hydrobromide has been prepared by the reaction of potassium phthalimide with ethylene bromide, followed by hydrolysis,1 by the addition of hydrogen bromide to ethyleneimine,2 and by the present method.3... 

A solution of 615 g. (3 moles) of /3-bromoethylamine hydrobromide (p. 13) and 416 g. (3.3 moles) of anhydrous sodium sulfite (u. s. p.) (Note) in 2400 cc. of water is concentrated on the steam bath to a minimum volume (thirty-six to forty-eight hours). After the mixture has cooled, the cold moist cake is triturated with 1500 cc. of concentrated hydrochloric acid and collected on an asbestos mat in a Buchner funnel. The precipitate is washed ten times with 150-cc. portions of concentrated hydrochloric acid. The filtrate is mixed well, decanted from precipitated salts if necessary, and concentrated over a free flame to a volume of 600 cc. 

Condensation of 2-bromoethylamine hydrobromide with benzoyl chloride in benzene in the presence of 5 equivalents of EtsN gave 2-phenyl-4,5-dihydrooxazole (1) in 67% yield [1]. Treatment of 1 with 3 equivalents of NBS in boiling CCL in the presence of AIBN led to 5-bromo-2-phenyloxazole (2). Presumably, sequential bromination and dehydrobromination of 1 led to 2-phenyloxazole, which underwent further bromination to afford 2. 

Ethylenimine has been prepared from /8-bromoethylamine hydrobromide by reaction with silver oxide, potassium hydroxide, or sodium methoxide from j3-chloroethylamine hydrochloride by reaction with sodium methoxide or sodium hydroxide and from 8-aminoethylsulfuric acid by reaction with sodium hydroxide. ... 

A frequently used method for the construction of the 2-amino-2-thiazoline ring (60) involves the reaction between thiourea and 2-bromoethylamine hydrobromide.122-124 If the amine nitrogen atom is... 

Oxo-l,2X5-azaphosphctanes 42 can be synthesized via an intramolecular Arbuzov reaction of A-2-chloroethyl amidoesters of P(m) acids proceeding under distillation in vacuo (Scheme 22) [43], The starting substrates were obtained in turn from diethyl-chlorophospite addition to aziridines. Subsequently, the reaction of dialkylchloro-phosphite and 2-bromoethylamine hydrobromide in 2 1 ratio in the presence of... 

Bromoethylamine 454 A-(2-Bromoethyl)phthalimide (20 g) is heated with concentrated hydrobromic acid ( /1.49 50-60 ml) in a bomb tube for 2h at 180-200°. Cold water is added to the cooled product, residual phthalic acid is filtered off, and the filtrate is evaporated to dryness on a water-bath. The dark residue solidifies on cooling and is recrystallized from anhydrous ethanol (15-20 ml). 2-Bromoethylamine hydrobromide forms dense crystals on cooling, but these are accompanied by a fine powder the latter is freed from mother liquor by decantation and crystallized again from ethanol. The hydrobromide, m.p. 155-160°, gives an unstable free base when treated with concentrated potassium hydroxide solution. 

Thioxo-l,3,6-thiadiazocin-5-ones (36) are conveniently prepared from a-amino acid ester hydrochlorides in one pot by sequential treatment with carbon disulfide, followed by 2-bromoethylamine hydrobromide (Scheme 28) <90SC2675>. Starting with L-tyrosine leads to an optically active thia-diazocine indicating that racemization does not occur during the reaction. 

Now, pantetheine itself (Scheme 12.110) was synthesized from the lactone that is, as shown in Scheme 12.110, when the easily oxidized thiol 7V-P-alanyl-2-mercaptoethylamine reacted with the chiral pantolactone in the absence of solvent at 100°C, pantetheine formed. The formation of the thiol 7V-P-alanyl-2-mercaptoethylamine and the reaction to form pantetheine began with the reaction of 2-bromoethylamine hydrobromide with benzylthiol. 

First, the 2-azanorbomene precursor, 108, is obtained by the aqueous imino Diels-Alder reaction between cyclopentadiene and the iminium ion derived from formaldehyde and 2-bromoethylamine hydrobromide. Exposure of a solution of amino bromide 108 to silver triflate provides the spiroaziridinium salt, 109, in good overall yield. The ability of 109 to function as an alkylating agent has been demonstrated with a variety of enolates [37]. 

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