close

Вход

Забыли?

вход по аккаунту

?

Патент USA US2404560

код для вставки
Patented July ‘23, 1946
2,404,560
‘UNITED STATES PATENT OFFICE
2,404,560
SULPHONES AND METHOD OF PREPARING
SAME
Louis L. Bambas, Grosse Pointe Woods, Mich., as
signor to Parke, Davis & Company, Detroit,
Mich., a corporation of Michigan
No Drawing. Application June 13, 1944,
Serial No. 540,137
3 Claims. (Cl. 260-239-6)
2
1
sulphate and others that are readily available to
The invention relates to the preparation of
sulphones useful for their therapeutic properties.
give the corresponding 2-imino-3-alkyl-4'-ami
More particularly the invention relates to com
no-5-thiazolonylphenyl sulphone.
‘ What I claim as my invention is:
pounds having the following general formula
1. A 2-imino-3-loWer-alkyl-4’-amino—5-thiazo
lonyl-phenyl sulphone having the formula
ll
ENGSOFC\ S / 0=NH
whereR is a, lower alkyl.
'
.
In my application, Serial No. 540,135, ?led June 10
13, 1944, I have disclosed a method for the prep
where R is a lower alkyl.
aration of 2'-amino-4’-nitro-5-thiazolylphenyl
sulphone having a melting point of 230-232” C.
and the formula
;
2. 2-imino-3-methyl-4'-amino-5 - thiazolonyl -
phenyl sulphone having the formula
15
S
3. The process for preparing a 2-imin0-3
Th'e compounds of the present invention may
be prepared by‘reacting the above mentioned
compound in the manner hereinafter set forth.
lower-alkyl-4'-amino-5 - thiazolonylphenyl
Example.—Preparation of 2-imino-3-methyl-4’
nitro-5-thz'azolonylphenyl sulphone
tro-5-thiazolony1phenyl sulphone having the for
mula
180 grams of 2-amino-4'-nitro-5-thiazolonyl
phenyl sulphone is heated with 270 grams of di
methyl sulfate on a water bath for 1 hour. The
reaction mixture is suspended in water and'heat
ed'to boiling (95-100° 0.). The crude 2-imino-3
methyl-4'-nitro - 5 - thiazolonylphenyl sulphone
sul
phone which comprises reacting v2-amino-4J-ni
'
~
HC—-—-N
OnNGSOrg (“J-NH:
with a di-lower alkyl salt to form 2-imino-3
30 lower-alkyl-4'- nitro - 5 - thiazolonylphenyl sul
phone having the formula
thereby obtained is reduced with 80 grams of am
monium chloride and 200 grams of reduced iron
in 2 liters of water at 80° C. for 1 hour. Care is
taken that the temperature does not rise above
S
80° since the desired compound is relatively un 3 5
stable at these temperatures. The sludge is
and reducing the latter to obtain 2-imino-3
cooled and the product is extracted from the
lower-alkyl-4’-amino - 5 - thiazolonylphenyl sul
iron with‘ alcohol. It is recrystallized from hot
phone having the formula
dilute alcohol (30%) to give 2-imino-3-methyl
4'-amino-5-thiazolonylphenyl sulphone which on 40
s
‘In the above example, instead of using dimethyl
sulphate, one can use the halide such as methyl
iodide or other dialkyl compounds such as diethyl
H(|f'—-N—R
mN-Osm-o \ /(lJ=NH
heating blackens at 160° C. and melts at 209-210°
C
where R is a lower alkyl.
5
LOUIS L. BAMBAS.
Документ
Категория
Без категории
Просмотров
0
Размер файла
91 Кб
Теги
1/--страниц
Пожаловаться на содержимое документа