DE292284C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

In addition to the large number of compounds of Hexamethylenetetraniins with organic Acids and acid derivatives are so far only rarely used therapeutically salts of the Base known with inorganic acids.

It has now been found that hexamethylenetetramine with superchloric acid to one Salts that are easily soluble in water, that are stable in the air, that react acidic, the hitherto unknown ίο hexamethylenetetramine perchlorate:

(CH ₂ ) ₆ N ₄ .HC1O ₄

united, and that this compound can be easily converted into the water-insoluble, also previously unknown dibromo- or diiodohexamethylene tetramine perchlorate can be convicted. The compounds have a strong antiseptic effect and show high resistance and are completely insensitive

ao against shock and blow, which is all the less was to be expected than according to the literature (see Beilstein, Handbuch der organic Chemistry, 1901, supplementary volume I, P. 643) the corresponding dichromate is said to be extremely explosive.

The easy solubility of hexamethylenetetramine perchlorate, combined with its acidic Reaction, distinguishes it in an advantageous way from the neutral, partly sparingly soluble Alkali perchlorates, while its air resistance to the other perchlorates, all of which, with the exception of the ammonium salt, are deliquescent (see Gmelin and Kraut, Handbuch der inorganic Chemie, 7th ed., Vol. I, II. Abt. [1909], p. 159), there are significant advantages.

The compounds are intended to be used for therapeutic purposes.

Hexamethylene tetramine perchlorate.
Example 1.

ι Mol. Hexamethylenetetramine is dissolved in a sufficient amount of water and with ι Mol. Superchloric acid (in the form of a 20 percent aqueous solution) added. Then a little alcohol is added and strongly cooled. That turns out to be nicely trained Salt which separates out crystals is filtered off with suction and dried.

Example 2.

ι mol. Hexamethylenetetramine chlorohydrate (or sulfate, nitrate, etc. or 1 mol. Hexamethylenetetramine and ι Mol. The corresponding acid) is in aqueous solution with 1 mol. a salt of the superchloric acid reacted with an inorganic base and the resulting Hexamethylenetetramine perchlorate by fractional crystallization from the inorganic Salt separately.

Melting point 158 °.

Analysis:

(CH ₂ ),., N ₄ • H Cl O ₄

72.00 =
13. ¹ O =

56.04
35.46

= N ₄
= Cl

calculates percent

29.93;

5.44; 23.29;

14.74;

found percent

30.10;

5.54;

23.56;

14.50.

Dibromohexamethylenetetramine

perchlorate. · ·

Example 3.

1 mole of hexamethylenetetramine perchlorate is mixed with 1 mole of bromine in aqueous solution. The deposited light yellow precipitate is filtered off with suction and dried.

Melting point 148 ° with decomposition.

j Diiodohexamethylenetetramine

perchlorate.

Example 4.

ι Mol. Hexamethylenetetramine is in aqueous solution with an alcoholic solution of ι mol. Iodine added, the separated red-yellow precipitate filtered off with suction and dried.

Decomposition point at about 120 °.

Analysis:

/ _ΓΗ ) μ R ,. π π η calculated (CH ₂ J ₁₁ N ₄ Bi ₂ -IIClO., _percent

72.00 =

5ö! O4 =

159.84 =

34.46 =

C ₆
H ₁₃

N ₄

Br ₂

Cl

17.98;

3.27;

13.99;

39.92;

8.86;

found percent

17.68; 3.25;

9.20.

Analysis:

(CH ₂ ), -, N ₄ I ₂ -H Cl O ₄

72.00 = C ₆
13.10 = H ₁₃
56.04 = N ₄
253.84 = J ₂
35.46 = Cl

calculates percent

14.56; 2.65;

11.33; 51.34;

found percent

14.83;

2.74; 11.54; 51.55;

7.43

Claims (1)

Patent claim: Process for the preparation of derivatives of hexamethylenetetramine, consisting therein that hexamethylenetetramine is converted into the superchloric acid salt by the customary salt formation methods and if necessary, this treated in solution with bromine or iodine.