SU468398A3 - The method of obtaining 4-amino-3,5-dihalophenylethanolamines - Google Patents

Description

The acids used for converting free bases to salts are predominantly hydrochloric, hydrobromic, sulfuric, phosphoric, lactic, citric, tartaric, maleic, or fumaric acid,

Oxazolidone teaches as follows

Example 1. 5- (4-amino-3,5-dichlorophenyl) -3-tert.-butyl-oxazolidone- (2). 2.8 g of 5 (4-amino-phenyl) -3-tert.-butyl-oxazolidone (2) (m.p .: 102-104 ° C) is dissolved in 50 cm of glacial acetic acid in 2 cm of water, and stirring, a solution of 3.9 g of bromine in 1O cm of glacial acetic acid is added dropwise in a few minutes. After 15 min. the reaction mixture is diluted with 250 cm of water, extracted twice with chloroform. The organic phase is shaken with water, dried with sodium sulfate and concentrated. The residue is dissolved in a small amount of ethyl acetate and the addition of 5- (4-amino-3, 5-dibromophenyl) -3-tert-butyl-oxazolidone- (2) petroleum ether (2) is brought to crystallization; mp: 118.5-12 ° C.

In the same way, the following oxazolidones are prepared by bromination or chlorination:

1.5- (4-amino-3,5-dichlorophenyl) -3-tert. -Butyl-oxazolide- (2) obtained by chlorination of 5- (4-amino-phenyl) -3-tert.-butyl-oxy azolidone- {2), mp .: 109-111 С

2.3-ethyl-5- (4-amino-3,5-dibromophenyl) -oxazolidone- (2), obtained by brominated 3 EGIL-5- (4-amino-phenyl) -oke azolidone- {2), t. square 112-113 0;

3.5- (4-amino-3,5-dibromo-phenyl) -3-methyl-oxazo-dol- (2) obtained by bromination with 5- (4-amino-phenyl) -3-methyl-oxazolidon- (2), m.p . 95-97 ° C.

4.5- (4-amino-3,5-dibromophenyl) -keazolidone- (2), prepared by brominating 5- (4-amino-phenyl) -oxazolidone- (2), mp. 167169, 5 ° C;

5.5- (4-amino-3,5-dichloro-phenyl) -ox-zolidone- (2), obtained by chlorination of 5- (4-amino-phenyl) -oxazolidone- (2), so pl. 157-159 ° C.

Example 2. The target products 1 are obtained as follows:

a) 1-4-amino-3,5-dichlorophenyl) -2-tert. -butyl-amino-ethanol.

1 g (0, ОЗЗЗ mole) of 5- (4-amino-3,5-dichlorophenyl) -3-tert.-butyl-oxazolidone- (2) is dissolved in 2 O cm of isopropanol

and add 2 cm of water and 2 g of potassium hydroxide. The resulting biphasic solution is boiled for 24 hours under reflux and then adding a small amount of ethanol and 1- (4-amino-3, 5-dichlorophenyl) -2-tret-butyl-amino-ethanol water is brought to crystallization . Output 0.80 g (87.4% of the theoretically possible mp. 11b-119 ° С.

Molecular weight: 277.20 Calculated,%: C 52.01 H 6.55 N1 O, 1 O ce 25.27

 2 2 Found: 51.7О

6.40 9.85 25.00

In the same way, the following compounds of the general formula 1 are prepared by souring or alkaline saponification of the corresponding oxazolidones:

1. 1- (4-amino-3,5-dibromophenyl) -2-tert-butyl-amino-ethanol; m.p. hydrochloride: 219.5-220 ° C (decomposition); obtained by alkaline saponification of 5- (4-amino-3,5-dibromophenyl) -3-tert-butyl-oxazolido- (2);

2.2-ethylamino-1- (4-amino-3,5-dibromophenyl) -ethanol, m.p. hydrochloride: 174175 ° C (decomposition), obtained by acidic saponification of 3-ethyl-5- (4-amino-3,5-dibromophenyl) -oxazolidone- (2);

3.1- (4-amino-3,5-dibromophenyl) -2-methylamino-ethanol, m.p. hydrochloride: 21021 .6 ° C (decomposition), obtained by acid saponification of 5- (4-amino-3,5-dibromophenyl) -3-methyl-oxazolidone- (2 J;

4. 2-amylo-1- (4-ami-no-3,5-di-bromo-phenyl) -ethanol, m.p. 214-216 ° С (decomposition), obtained by alkaline saponification of 5- (4-amino-3, 5-dibromophenyl) -okol dono- (2).

5. 2-amino-1- (4-amino-3,5-dichloro-phenyl) -ethanol, m.p. hydrochloride: 199-2О4 ° С (decomposition), obtained by alkaline saponification of 5- (4-amino-3,5-dichlorophenyl) -oxazolidone- (2).

Claims (1)

Invention Formula The method of obtaining 4-amino-3,5-dihalo60 of phenylethanolamines of the general formula: 5 OH Hal-j CH-CH2-N Hal where Hal is chlorine or bromine; R ' is hydrogen or alkyl with 1-5 carbon dioxide atoms or their salts, characterized in that, in order to increase the yield of the target product, oxazolidone of the general formula: 468398 6 O. e. IJI u i n where Hal and R - have the indicated meanings, are hydrolyzed in the usual way, for example with an alkali metal hydroxide, followed by isolation of the target product by a known method as a base or salt.