SU576919A3 - Method of preparing derivatives of butyric acid amide - Google Patents

Description

(54) METHOD OF OBTAINING AMIDA DERIVATIVES OF OIL ACID

The invention relates to a process for the preparation of new compounds, derivatives of butyric acid amide, which have an anti-inflammatory effect.

These compounds have the formula

x, /

.OVtHr Hr H, -C-N,

-a, GO

,, v v

where L is hydrogen or chlorine, X | - chlorine, L2 hydrogen or alkyl pa; d1kal, sodermsac 1-5 carbon atoms, RI - hydrogen or an alkyl radical containing 1-5 carbon atoms, R2 - pidpoksil or alkoxyl group, containing 1-5 atoms of yi-lerod.

The precut method is based on the well known reaction of the reaction of ylotslot chlorides with amines 1.

In order to obtain these compounds, chloraigi.ceride K1 slots are suggested.

TO.

i-CHr KrCHrC- / С

expose the action of a general formula

HN-- 2 where X, Vi, X, RI nRj have the indicated values

in the environment of aromaggggsky hydrochloride, simple ether or dimethylformamide at 0-20 ° C.

According to the previous method, target ones are obtained. up to 92%,. Example 1. 4 - (W - l - sorbenzoyl - 2

mgtnl feyush - N - methoxyamide oily Juice.

C. Mixed South 4 - (3 p Chloro 6 H 2 X 2 methyl) - butyric acid and 30 cm of chloride. Slowly heat the mixture from -80 ° C to vydelskuyut at this tera-ture to npexp-iit eNIL alter the gases, then remove the excess SOCIj BbinapiiBajmeM and distillation with benzene. The remainder of the solution is Goth E 50 cm and later heals the right. A batch of a1b is added: n solution to a mixture of 9.5 cm about -Mgtilgitsroksilam-Chesh 50 cm of benzene, extract temperature approx. 10 ° C, allow to stand for half an hour, remove f.chltrandig sediment n evaporated oizol. The residue is purified by dissolving in toluene, by adding petroleum in a throat

STOLNSH1, a for .CM cooling and.; (Ttlsl mt (Wc - xjiopCJeijsouji - 2 - methyl) - fechp N metoccles of butyric acid, yield 97%; mp 104 - 105 ° С

Bb: iL4Cj euo,%: C 65.98; And 5.83; Ct 10.25; N 4.05.

% Ideio,%: C 65.9; Ы 5,8; C) 10.1; M 4.1.

PRI mme R 2. 4 - (W - n chlorobenzoyl - 2

) - feksh - N methyl - N - metoksnamid Mayach 1yu acid.

 Shalogiche way, from the. San in the example

1, feed, take chloraigi) feed 4

(S - n. Chlorobenzoip - 2 - methyl) fesh

butyric acid with N - o - Sh1mg pshhydroxylamine in tetragvdrofuran, get 4 - (3 - and -chlorobyoyl 2 - methyl) - phenyl N - metheshch - N. methoxyd

chromatographic method on silusagel,

elutro CTviecbro methyl chloride - acetone (4) "

The product is characterized in this system, 5,

yield 80%. .

Bmisleno,%: C, 66.75; H 6.16; N 3.89; Ci 9.85.

Nano,%: C, 66.8; H6.1; N4.0; Ct SD. Example 3: 4 - (3 - n chlorobenzoyl - 2 methyl) feiyl - N hydroxyamide of butyric acid.

Similar to the method described in example 1,

interacting above tsazany hlorangidrvd with pschroksilaminom in lilformamide,

4 - (3 - n - chlorobenzoyl - 2 - methyl) phenyl - N - hydroxy Q D butyric acid is obtained.

The product is recrystallized from benzene; m.p. 125 ° C, yield 48%. .

Calculated,%: C 66, 15; H 5.45; N 4, 23; From 10.69.

Found,%: C 65.2; H 5.5; N 4.3; C1 10.9.

EXAMPLE 4. 4 - (3 - n chlorobeisoyl - 2-methyl) - phenyl - N - hydroxy - N - megalamide of butyric acid.

Analogously to the method described in example 1, by reacting the above acid chloride with the N – mellumine oxides of the boil in a mixture of benzene – dimethylformamide (5; 1), 4 - (3 - n - chlorobenzoyl. 2. Methyl) - phenyl - N hydroxy is obtained. - N - methylamide of butyric acid, which is purified by washing with hexane and recrystallization in isopropyl ether x; yr1 C1i.y methylene (7: 3), t. Il. 116, yield 85%,

Vymksleno, 9 ": C65.99; H5.83; N4.05; C1 10.25.

Found,%: C 66.1 ;, and 5.8; N 3.9; C1 10.2.

Claims (1)

1. Buhler Co. and others. Organic syntheses M 1973,0.388.