DE1193947B - Process for the preparation of dihydro-1, 3, 5-dithiazine compounds - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY Int. α .:

C07d

GERMAN

PATENT OFFICE

DESIGN SCREEN

German class: 12 ρ - 4/01

Number:
File number:
Registration date:
Display day:

D41840IVd / 12p
June 26, 1963
June 3, 1965

The subject of the main patent 1 162 841 is a process for the preparation of dihydro-1,3,5-dithiazine compounds the general formula

CH ₈

CH ₂ CH ₂ \ /

Process for the preparation of dihydro-1,3,5-dithiazine compounds

Addendum to the patent: 1162 841

in which R can be, inter alia, an alkyl radical substituted by an aryl, hydroxyl, hydroxyalkyl or carboxyl group. These compounds are prepared by reacting formaldehyde or formaldehyde-yielding substances and a primary amino compound of the general formula H ₂ NR with hydrogen sulfide in an alkaline medium or with alkali hydrogen sulfide.

It has now been found that dihydro-1,3,5-dithiazine compound of the above general formula, in which R is an alkyl radical substituted by an alkoxy or sulfonic acid or alkali metal sulfonate group, is obtained by reacting formaldehyde or such supplying substances and a primary Amino compound of the general formula H ₂ NR can be prepared with hydrogen sulfide in an alkaline medium or with alkali hydrogen sulfide by the process of Patent 1,162,841 if a primary amine of the general formula H ₂ NR is used, in which R is an alkoxy or sulfonic acid - or alkali metal sulfonate group means substituted alkyl radical.

As formaldehyde-providing substances in the context of the invention, lower polymers of formaldehyde, z. B. paraformaldehyde can be used.

The starting materials are used in the presence of a solvent, e.g. B. water or aqueous lower aliphatic alcohols to. You can also use an alcohol alone as a solvent, e.g. B. methanol, use.

The reaction usually takes place at room temperature, but can also be at higher or lower temperatures Temperatures are carried out. It is advisable to use an excess of formaldehyde and alkali hydrogen sulfide or to use hydrogen sulfide. In most implementations it is irrelevant In which order the starting materials together-notifier:

German gold and silver separator
formerly Roessler,
Frankfurt / M., Weißfrauenstr. 9

Named as inventor:

Dr. Manfred Beck, Heidelberg-Boxberg;

Dr. Hans Wagner, Constance

are given; therefore difficulties caused by poor solubility of the starting or end products can easily be avoided.

example 1

g of sodium hydrogen sulfide (1 mol) are dissolved in 80 ml of water with stirring. To this solution is allowed at 15 to 20 ⁰ C 230 ml 39volumprozentige aqueous formaldehyde solution are added dropwise. 20 minutes after the addition, a solution containing 0.5 mol of taurine as the sodium salt is quickly added. The temperature rises to 30 to 34 ° C. The solution is stirred for a further 10 hours at room temperature. The precipitated reaction product is filtered off with suction. 99.5 g of the monohydrate of sodium 2- (5 ', 6'-dihydro-1', 3 ', 5'-dithiazino) ethane sulfonic acid are obtained.

Calculated
found

Sulfated ash

N 5.2%;
5.16%.

calculated as Na ₂ SO ₄ ... 26.4%;
found 26.7%

Example 2

56 g of sodium hydrosulfide (1 mol) dissolved in 150 ml of water are added (3 moles) with stirring at 15 to 20 ⁰ C 39volumprozentige ml aqueous formaldehyde solution. After 20 minutes of post-reaction

509 578/404

tion are added 40 g (0.5 mol) of methoxypropylcamine. The temperature of the reaction mixture rises from 20 to 30 to 35 in a few minutes ^; C. Stirring is continued overnight and the oily upper phase is then separated off with methylene chloride. After drying with sodium sulfate, hydrogen chloride is passed in with cooling. The hydrochloride of N-methoxypropyl-So-dihydro-1,3,5-dithiazine which separates out is filtered off with suction and dried.
Yield: 74.8 g; Mp. 129 to 130 ⁰ C.

Analysis:

Calculated
found

. S 27.9%. CI 15.4%;
. S 28.3%, Cl 14.9%.

Claims (1)

Claim: Process for the preparation of dihydro-1,3,5-dithiazine compounds of the general formula CH ₂ S S 1 i CH ₂ CH ₂ by reacting formaldehyde or formaldehyde-yielding substances and a primary amine of the general formula H ₂ NR with hydrogen sulphide in an alkaline medium or with alkali hydrogen sulphide according to patent 1 162 841, characterized in that a primary amine of the general formula H ₂ NR is used, in which R is an alkyl radical substituted by an alkoxy or sulfonic acid or alkali metal sulfonate group. 509 578/404 5.65 © Bundesdruckerei Berlin