DE266121C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

In further experiments it has been found that in the reaction of the main patent Use bromo- and chloroacetyl urethanes in place of the bromoacetylurea with good success let, and that here the reaction proceeds faster and smoother than in the process of the main patent. Except for the chloroacetyl urethane already described in the literature and bromoacetyl urethane, some other halo urethanes are prepared and described below.

So obtained by exposure to chloroacetyl chloride on methyl carbamic acid the methyl chloroacetylcarbamic acid, which is used in 145 ° melts.

If instead of chloroacetyl chloride, bromoacetyl chloride or bromoacetyl bromide is left on carbamic acid Act methyl, one gets in a smooth way the bromoacetylcarbamic acid methyl ester, which is close in its properties to the corresponding chlorinated ester and has its melting point at 148 °. The isobutyl chloroacetylcarbamic acid ester, which is formed by the action of chloroacetyl chloride on isobutyl carbamate, melts at 78 °, the isobutyl bromoacetylcarbamate shown similarly at 87 °.

These haloacyl urethanes can also be produced by the action of halo fatty acid esters to the corresponding 2V «urethanes are obtained.

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Using the example of the main patent, the reaction can be illustrated by the following Express equation:

C ₂ H ₆ O-CO-NH-CO-CH ₂ Br

+ NaCOO CH ₃

= C ₂ H ₆ O -CO -NH -CO-CH ₂ -OC-CH _Z + Na Br.

Example 1.

210 parts of bromoacetyl urethane and 136 parts Acetic acid sodium is refluxed with 1500 parts of high percentage alcohol for 4 to 6 hours cooked. After the precipitated sodium bromide has been filtered off, the alcohol is concentrated and the reaction product is allowed to crystallize out. The acetyl glycol urethane forms colorless needles, which melt blurred at 98 °. It is easily soluble in water like alcohol.

Example 2.

473 parts of sodium bromoisovaleric acid and 525 parts of bromoacetyl urethane are added 2500 parts of high percentage alcohol cooked according to Example ι and processed further. That Bromisovalerianylglykolylurethan forms colorless needles which melt at 103 °. It is sparingly soluble in water, but it is easily absorbed by fuel and ether.

Example 3.

160 parts of sodium salicylate and 210 parts

Bromoacetyl urethane are made with 1500 parts of alcohol cooked and processed in the manner described in Example 1. The salicylic acid glycolyl urethane crystallizes on cooling

. off, is suction filtered and washed with water to remove the sodium bromide.

The body melts at 146 ⁰ , is insoluble in water and ether, easily soluble in warm alcohol.

Example 4.

203 g of sodium bromide valerate and 800 g of alcohol abs. are with 151 g of chloroacetylcarbamic acid methyl ester Boiled for 3 to 4 hours on the reflux condenser, the precipitating common salt is filtered off and the Lye somewhat concentrated. The methyl bromoisovalerylglycolylcarbamic acid crystallizes from the concentrated liquor and melts at 90 °, it is soluble in fuel and ether, but insoluble in water.

Example 5.

160 parts of sodium salicylic acid are mixed with 151 parts of methyl chloroacetylcarbamic acid Boiled in about 1000 parts of fuel for a few hours, the lye evaporated from the table salt freed and set aside for crystallization. The salicylic acid glycolylcarbamic acid methyl ester is quite easily soluble in water and alcohol and melts at 150 °.

In the above reactions, benzene or toluene can also be used instead of alcohol.

Claims (1)

Patent claim: Modification of the process for the production of Derivatives of glycolic acid acid, characterized in that for the purpose of production the glycolyl urethane bromine or chloroacetyl urethane and the salt of an organic one Allow acid to act on each other using suitable solvents.