SU362022A1 - METHOD FOR OBTAINING PHOSPHOLYLATED THIOSEMICARBAZONES - Google Patents

Description

one

The invention relates to the field of phosphorus-containing chemical compounds and can be applied to the preparation of thiosemicarbazone alkylalkoxyphosphinylacetic aldehydes of the general formula

R

PCH2CH N-NH-c; -NH2

RO

/ Iiii

OS

alkyl or allyl; R is alkyl.

R

The method for producing phosphorylated thiosechmicarbazones, as well as the compounds themselves, has not been described in the literature. They can be used as potential antimicrobial agents, especially since non-phosphorylated thiosemicarbazones have such properties. The interaction of aldehydes with thiosemicarbazide to produce thiosemicarbazones is widely known. However, phosphorylated aldehydes were not previously involved in such a reaction.

The proposed method consists in the interaction of thiosemicarbazide with phosphorylated aldehydes in an organic solvent medium, followed by isolation of the target product by known methods.

Example 1. Thiosemicarbazone allyl ethoxyphosphinylacetic aldehyde.

A solution of 1.7 g of allplathoxyphosphine-aldehyde aldehyde in 17 ml of ethyl alcohol is placed in a flask with a ground-in stopper and a hot solution of 0.8 g of thiosemicarbazide in 17 ml of water is poured into it. The reaction mixture was kept at room temperature for one day and then cooled to. The precipitated crystals are filtered and recrystallized from a 50% aqueous stage. Obtain 1.3 g (54% of theory) of thiosemicarbazone allyl ethoxyphosphinyl acetic aldehyde, t. Pl. 122-123 ° C.

Found,%: P 12.40, 12.17; N 16.45, 16.92.

CsHieNaOsPS. Calculated,%: P 12,44; N 16.96.

Example 2. Thiosemicarbazone ethylethoxyphosphine aldehyde.

Under similar conditions, 1.1 J (61%) of thiosemicarbazone ethyl ethoxyphosphine acetic aldehyde was isolated from 1.3 g of ethylethoxyphosphinyl acetic aldehyde dissolved in 13 ml of ethanol and 0.72 g of thiosemicarbazide dissolved in 13 ml of water. 152.5 ° C.

Found %: P 12.96, 13.30; N 17.95, 18.10. CrHieNsOsPS.

Calculated,%: P 13,08; N 17.72.

Example 3. Thiosemicarbazone allylisopropoxyphosphinylsaldehyde.

Under analogous conditions, 1.7 g of allylisopropoxyphosphinyl acetic aldehyde, dissolved in 17 ml of ethanol, and 0.8 g of thiosemicarbazide dissolved in 17 ml of water, after recrystallization from benzene, 0.8 g (40%) of thiosemicarbazone allylisopropoxy peg syphylfyne hydroxyphenylsulfyl nitroxyfine hydroxyphenylsulfolyl acetate were obtained. pl. 125-127 °. Found,%: P 11.97, 12.07; N 15.82, 15.92. CgHisNsOaPS. Calculated,%: R 11.78; N 15.96. 4. Subject of the invention. A method for producing phosphorylated thiosemicarbazones, wherein phosphorylated aldehydes are reacted with thiosemicarbazide in an organic solvent medium, followed by separation of the target product by known methods.